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    • 专利摘要:
    Novel Pyridyl substituted thiazolidine and 1,3-thiazine derivatives having utility as plant fungicides, and terrestrial and aquatic plant growth regulators, with the formula <CHEM> wherein R is C3-C10alkyl, C3-C8-cycloalkyl, methallyl, phenyl, halophenyl, trifluoromethylphenyl, benzyl, methoxybenzyl, methylbenzyl, halobenzyl, dimethylaminoethyl, methylcyclohexyl, C3-C8cycloalkyl(C1-C3)alkyl, alpha -methylbenzyl, 2-thiazolyl, nitrophenyl, phenoxyphenyl, (tetrahydro-2-furanyl)-methyl, haloanlyl, trifluoromethylthiophenyl, methylthiophenyl, 2-norbornyl, furfuryl, 2-(1-methoxypropyl), methoxyphenyl, fluoro(C1-C2)alkoxyphenyl, 3-4-(methylenedioxy)phenyl, xlyl, biphenylyl, tolyl, or halotolyl; X is oxygen or sulfur; <CHEM> R<1> is hydrogen, methyl, or -S(C1-C6alkyl); R<2> is hydrogen, C1-C6alkyl, or -S(C1-C6alkyl); R<3> is hydrogen or methyl; R<4> is hydrogen or C1-C6alkyl; and R<5> is hydrogen or methyl. Methods for their preparation are described, e.g. 4-chloroaniline was reacted with 3-pyridine carboxaldehyde and the reaction mixture was reacted with thiolactic acid to give 3-(4-chlorophenyl)-5 -methyl-2-(3-pyridyl)-4-thiazolidinone.
    公开号:SU1079175A3
    申请号:SU792831951
    申请日:1979-10-15
    公开日:1984-03-07
    发明作者:Виктор Крумкалис Эрикс
    申请人:Эли Лилли Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of new heterocyclic compounds, namely, 4-thiazolidine compounds of the general formula H C-C-B II where R, is C-C-alkyl, C-Cd-cycloal kil, metal, phenyl, halophenyl, trifluoromethylphenyl, methoxybenzyl, methylbenzyl, halobenzyl, dimethylaminoethyl, methylcyclohexyl, cyclohexylmethyl,. 1- (2-cyclopentyl-1-methyl) -ethyl, oi-methylbenzyl, 2-thia lyl, nitrophenyl, phenoxyphenyl, (tetrahydro-2-furanyl) -methyl, trifluoromethylthiophenyl, 4-methylthiophenyl 2-norbornyl, furfuryl, 2- (1-methoxy) propyl, methoxyphenyl, tetrafluoroethoxybenzyl, xylyl, tholyl, halothyl or halophenylamino, or 3,4- (methylenedioxy) benzyl, R2 - hydrogen; C, -C-alkyl or methylthio radical; R-J is hydrogen, methyl or methylthioradkkal, possessing fungicidal activity and properties of plant growth regulator. Compounds of general formula D can be used in agriculture. A known method for producing thiazolidinones of the general formula. y-O where R (is hydrogen or chlorine, hydroxy or carboxyl, which consists in reacting benzaldehyde with the corresponding substituted aniline at the boiling point of the reaction mixture to remove water in benzene, followed by reacting the resulting product with thioglycolic acid at boiling point of the reaction mixture with removal of the reaction water 1. The purpose of the invention is to obtain new thiazolidinone derivatives, which can be used in agriculture as substances possessing the fungicidal activity and properties of the plant growth regulator. The aim is achieved according to the method for preparing compounds of general formula 1, which consists in reacting the 3-pyridylcarbgdehydehyde with a substituted amine of the general formula where R has the indicated values, followed by the interaction of the obtained product with thioglycol or thiolactic acid, or the desired product, where R 2 is hydrogen and R is methyl, is converted by alkylation to the desired product, where R g is alkyl, or the desired product, where R.-z and R are hydrogen, water into the desired product, where R and / or R-) - metiltioradikal. When R-OH is a sterically hindered amine, the process is carried out in the presence of a cyclizing agent. Example 1.3- (4-chlorophenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone. In a round three-necked flask equipped with a refrigerator, a Dean-Starn trap and a mechanical stirrer, 25.4 g (0.27 mol) of 4-chloroaniline and 250 ml of toluene are placed. While stirring, 21.4 g (0.27 mol) of 3-pyridinecarboxaldehyde is added to this solution and the reaction mixture is boiled until the calculated amount of water (, 6 ml) is accumulated in the Dean-Stark trap. The hot reaction mixture is cooled to An excess of thiomolic acid is added to it at room temperature, the total amount of which is 30 g, after which the reaction mixture is boiled again until the Dean-Stark trap stops. This requires about 4 hours of aging with boiling. Next, the reaction mixture is cooled and concentrated in vacuo to dryness. The solid residue is recrystallized from a mixture of hot diethyl ether and acetone to obtain a product, the melting point of which was approximately i20-i22 ° C, and which, according to IR spectral, NMR spectral and elemental anashis identified as 3-C47-CHLORPHENYL) -5-methyl-2- (3-pyridyl) -thiazolidinone. Product weight is 7 g. Elemental analysis data. Found,%: C 59.23; H 4.26; N 9.19. C, y} ;, C {N.20S .. Calculated,%: C 59.11) H 5.30, N 9.19. Example 2. 3- (2,4-difluorophenyl) -2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately 125-127 seconds. It is prepared from 13 g of 2,4-difluoroaniline, 10 g of 3-pyridylcarboxal & degid and 13 g of thioglycolic acid. Product weight 15 g. Elemental analysis data. Found,%: C 57.80; H 2.68; N 9, 61. CH H. Calculated,%: C 57.53, H 2.45; N 9.58. Example 3. 3- (2-fluorophenyl -2- (3-pyridyl) -4-thiazolidin6n .. Melting point was approximately 142-143s, obtained from 15 g of 2-ftsraniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight Elemental analysis data found,%: C 61.50; H 4.34 N 10.07. C, 4H "Calculated,%: C 61.30; n 4.04; N 10.21. 4. 3 -Nonyl-2- (3-p Example of Ridyl) -4-thiazolidinone .. Melting point was approximately 82-83 ° C, prepared from 11.2 g of N-nonylamine, 15 g of 2-pyridylcarboxaldehyde and 13 g of thio colic acid . Product weight 2, Elemental analysis data. Found,%: C, 66.33; H, 8.22; N, 8.85. C, 68.62 ; H 8.55-, Calculated,%: N, 9.14. Example 5. 3- (4-chlorobenzium -2- (3-pyridyl) -4-thiazolidinone. Melting point was approximately obtained from 15 g of 4-chlorobenzylamine , 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 20 g. Data of elemental analysis. Found,%: C 58.78, H 4.42, N 8.89., C, 5H ,, Calculated,% : C 59.11; H 4, 80; N 9.19. Example 6. 3-Cyclopentyl-3- (3-pyridyl) -4-thiazolidinone. The melting point was approximately 118-119 s. I get from 12 g of cyclopentyl-1-1, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 6.5g. Elemental analysis data. Found,%: C 63.01, H 6.21; N lf, 19. C | jH ,, R-OS Calculated,%: C 62.87; H 6.49, N11.2. Example 7. 3-Phenyl-2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately 177-178s, prepared from 13 g of aniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 9 g. Elemental analysis data. Found,%: C 65.44; H 4.89; .N 10.76. Calculated: C 65.60 / H 4.72; N 10.93. Example 8. 3- (2-Metapyl) -2- (3-pyridyl) -. 4-thiazolidinone. The melting point is approximately obtained from 15 g of 2-metallamine, 20 g of 3-pyridylcarboxaldehyde and 20 g of thioglycolic acid. Product weight 23 g. Elemental analysis data. Found,%: C 61.56; H 5.90; N 11.70. C 1-2 H 13 N2 OS Calculated,%: C 61.54; H 5.98, S 11.97. Example 9. 3- (1-Methylhexyl) -2- (3-pyridyl) -4-thiazolidine. The melting point is approximately 67 ° C, prepared from 16 g of 2-aminoheptane, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 3 g. Elemental analysis data. Found,%: C 64.70; H 7.76; N 9.97. CijHxjjN-OS Calculated,%: C 64.71 / H 7.97, N 10.06. PRI me R 10. 3- (3-Chlorophenyl) -2- (3-pyridyl) -4-thiazolidinone. The spinning temperature is about 154-155s, from 13 g of 3-chlorrraniline, 10 g of 3-pyridylcarboxaldehyde and 10 g of thioglycolic acid. Product weight 13 g. Elemental analysis data. Found,%: C 57.63; H 4.07; N 9.66. From 14 n. CrMgOB Calculated,%: C 57.83, H 3.81; N 9.63. Example 11. 2- (3-pyridyl) -3- (alpha, alpha, alpha-trifluoro-n-tolyl) -4-thiazolidinone. In the form of an oil-like product, 16 g of 3-trifluoromethylaniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid are obtained. Product weight 8g. NMR spectrogram (CDCpj). (delta): 3.9 (d,) 6.3 fS -C-lf), li-C H, 5 (t, phenyl, -CF), 8 Elemental analysis data. Found,%: C 55.79, H 3.56 / 8.75. C, UN “Calculated,%: C 55.55; H 3.42; 3.64. PRI m e. 3- (4-Fluorophenyl -2- (3-pyridyl) -4-thiazolidinone). Melting point of approximately 161 ° C, obtained from 55.5 g of 4-fluoroaniline, 53.5 g of 3-pyridylcarboxaldehyde and 46 g of thioglycolic acid . Product weight 70 g. Elemental analysis data. Found,%: C 61.08, H 4.15, N 10.17. ,, Calculated,%: C 61.30; H 4.04; N 10.21 Example 13. 3- (Cyclohexylmethyl- (2- (3-pyridyl) -4-thiazolidinone). Melting point is approximately obtained from 11.3 g of cyclohexamethanamine, 10 g of 3-pyridylcarboxaldehyde and 10 g of thioglycolic acid. Weight of product 15 d. It is identified by NMR data. Analysis 14. Example 14. 3- (3,5-Dichlorophenit1) -2- (3-pyridyl) -4-thiazolidinone. The melting point was approximately leO-iei C, obtained from 16.2 g of 3,5-dichloroaniline, g 3-pyridylcarboxaldehyde and 10 g thioglycolic acid. Weight product 11 g. NMR spectrogram (CDCe) (del ta) 3.9 (d, methylene), 6.2 (S, S l 7.2 (.,) 7.6, (,.), Cl, 8 jH). Example 15. 3- (2-Fluorobenzi -2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately from 12.5 g of 2-fluorobenzylamine, 10.7 g of 3-pyridylcarboxaldehyde, and 10 g of thioglycolic acid. Product weight 6 g. NMR spectrogram (CDCf,) (del ta) 3.9 g (S / S-CHj-C / c /), 4.5 (q., Benzyl), 5.5 (S, - C-ir) j7,. 8,8Yr ".jrt h Example 16. 3- (3,4-Methyl dioxybenzyl) -2- (3-pyridyl) -4-thia lidinone. The melting point is approximately 121-122 ° C, prepared from 15.1 g of piperonylamine, .11 g. 3-pyridylcarboxaldehyde and 14t thioglycolic acid, weight of product 4 g. Elemental analysis data Found,%: С -60.95, H 4.45; N 8.83. C, bN, 4K.dOZZ Calculated,%: C 61.13 H 4.49; N 8.90. Example 17. 3- {3,4-Dichlorophenyl) -2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately 160-162 ° C, prepared from 16.2 g of 3,4-dichloraniline, 11 g of 3-pyridyl carboxaldehyde and 14 g of thioglycolic acid. Product weight 14 g. Elemental analysis data. Found,%: C 51.54 H 2.96, N 8.54. C S Calculated: C 51.71, H 3.10; N 8.61 Example 18. 3- (2,4-Dichlorophenyl) -2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately 170-171 s, prepared from 16.2 g of 2,4-dichloroaniline, 12 g of 3-pyridylcarboxaldehyde and 12 g of thioglycolic acid. Product weight 4 g. Elemental analysis data. Found,%: C 51.52; H 2.90; N 8.62 Ci H oCEjNjOS Calculated,%: C 51.71) H 3.00 / N 8.61. Example 19. 3- (4-Chlorophenyl) -2- (3-pyridyl) -4-thiazolidinone. The melting point is approximately 149-151 ° C., prepared from 9 g of 4-chloroaniline, 7.5 g of 3-pyridylcarboxaldehyde, and 15 g of t-ioglycolic acid. Product weight 9 g. Elemental analysis data. Found,%: C 51.52; H 2.90; N 8.62. C | 4H, Calculated,%: C 51.71; H 3.00, N 8.61. Example 19. 3- {4-Chlorophenyl) .- 2- (3-pyridyl) i-2- (3-pyridyl) -4-thiazolIDYANON. The melting point is approximately 149-l5lc, prepared from 9 g of 4-chloroaniline, 7.5 g of 3-pyridylcarboxaldehyde and 15 g of thioglycolic acid. Product weight 9 g. Elemental analysis data. Found%: C 58.73; H 4.47; N. с, 4 Н „CENTOS Calculated,%: С 57.83; H 3.81, N 9.63. Example 20. 2- (3-Pyridyl - 3- З- (1,1,2,2-tetrafluoroethoxy) fnyl-4-thiaeolidinone, In the form of butter-like product is obtained from 21 g of 3-tetrafluoroethox aniline, 11 g of 3-pyridylcarboxal degida and 14 g thioglycolic acid. Product weight 4 g. NMR spectral analysis (CDCI. (delta) 3.9 (s, S — CHj — C (o)), 6.2 (S, —CN), 7.3 , Elemental analysis data Found:%: C 51.84 H 3.19, N 7.32. CibH F N-jOjS Calculated,%: C 51.61, H 3.25 / N 7.52. Example 21. 3-Cyclohexyl -2- (3-pyridyl) -4-thiazolidinone. The melting point was approximately llO-lll C, obtained from 10 g of cyclohexylamine, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic Islota. Prbduk weight 4.6 g. Elemental analysis data. Found,%: C 63.90; H 6.72; N, 10.44. C, fN (gNjOS Calculated,%: C 64.09, H 6, 92; N 10.68, Example 22. 3-Cyclopropyl-.- 2- (3-pyridyl) -4-thiaeolidinone. The melting point of approximately 112-113 ° C is obtained from 8 g of cyclopropylamine, 15 g of 3-pyridylcarboxaldehyde and 13 g thioglycolic acid. Product weight 16 g. Elemental analysis data. Found,%: C 60.11, H 5.32, N 12.55. C I, H Calculated,%: C 60.00; H 5.45, N 12.78. ff p m imep 23. 3-, 3-chloropheni-5-methyl-2- (3-pyridyl) -. 4-thioazole ion. The melting point was approximately 133 ° C; is obtained from is g of 3-chloroaniline, 15 g of 3-pyridium carboxaldehyde, and 13 g of thiolactic ACID. Product weight 9.5 g. Elemental analysis data. Found,%: C 53.98; H 4.26; N 9,10. c, 5H ,, ceN, Calculated,%: C 59.11; H 4.30; N 9.19. Example 24. 3- (2-Chlorophenyl) -2- (3-pyridyl} -4-thiazolidinone. The melting point is approximately 134 ° C, prepared from 18 g of 2-chloroaniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid . Product weight 4.6 g. Elemental analysis data. Found,%: C 57.49; H 3.74; N 9.32. C, 4H I, Calculated,%: C 57.83; H 3.81; (N, 9.63. Example 25) 2- (3-Pyridyl) -3- (4-tolyl) -4-thiazolidinone. The melting point is approximately 187 s, prepared from 15 g of i-toluidine, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 16 g. Data of elemental analysis Found:% C 66.79; H 5.13, N 10.58. C, yN, 4 LOBOB C 66.64; H 5.22, Calculated,%: 10.36. 26. 3- (4-Methoxy-Example Nile) -2- (3- pyridyl) -4-thiazolidinone. The melting point is approximately 144-145 ° C., obtained from 17 g of 4-methoxyaniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Weight of the product is 5 g. Elemental analysis data Found,%: C 63, 20 H 5.05; D 9.99. C 62.92; .H 4.93; Calculated,%; N 9.78. Example 27. 2- (3-Pnridyl) -3- (alpha, alpha, alpha-trifluoro-17-tolyl) -4-thiazolidinone. The melting point is approximately obtained from 16 g of 4-aminobenzotrifluoride, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid. Product weight 8g. Elemental analysis data. Found,%: C 55.15; H 3.41, N 8.85. C, 5-H I, Calculated,%: C 55.55; H 3.42, N 8.64. Example 28. 3-Hexyl-2 (Cppiridyl) -4-thiazolidinone. The melting point is approximately obtained from 12 g a-hexylamine, 11 g 3-pyridylcarboxaldehyde and 10 g thioglycolic acid. Product weight 21 g. Elemental analysis data. Found,%: C 63.52, H 7.47 / N 10.59. Calculated,%: C 63.60 H 7.63; N 10.60.
    Example 29. 3-Cyclohexyl-5-methyl-2- (3-pyridyl) -4-thiazolidinone.
    A melting point of approximately 10 g is obtained from cyclohexylamine, 10.7 g of 3-pyridylcarboxaldehyde and 10.6 thiollaminoic acid. Product weight 13 g.
    Elemental analysis data.
    Found,%: C, 65.40} H, 7.00;
    n 10.00.
    ClfH oNjOS
    Calculated,%: C 65.18, H 7.29, N 10.14.
    Example 30. 5-Methyl-3- (4-tolyl) -2- (3-pyridyl) -4-thiazolidinone.
    Melting point of approximately 170 s is obtained from 10.7 g of I-toluydine, 10.7 g of 3-pyridylcarboxaldehyde and 10.6 g of thiolactic acid. Product weight 18g.
    Elemental analysis data.
    Found,%: C 68.32 J H 5.29; N 9.86.
    C | 6 "I & 20S
    Calculated,%: C 78.06, H 5.00}
    S 9.92.
    Example 31. 3- (4-Chlorobenzyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone.
    in the form of an oil-like product, 10.7 g of 3-pyridylcarboxaldehyde and 10.6 g of thiolactic acid are obtained from 14 g of 4-chlorobenzylamine. Product weight 7.9 g
    Elemental analysis data.
    Found,%: C 60.42; H 4.61; N 8.59.
    CI HIJCIN OS
    Calculated,%: C, 60.28, H, 4.71 and 8.79.
    Example 32. 3- (2-chlorophenyl-5-methyl-2- (3-pyridyl) -4-thiazolidinone.
    The melting point is approximately equal to 12.7 g of 2-chloroaniline, 10.7 g of 3-pyridylcarboxaldehyde and 10.6 g of thiolactic acid. Product weight 600 mg.
    Elemental analysis data.
    Found: C 59.32; H 4.54, H 8.95.
    With I5H |,
    Calculated,%: C 59.11, H 4.30} N 9.19.
    Example 33. 5-Methyl-3- {1-methylhexyl) -2- (3-pyridyl) -4-thiazolidinone as an oil-like product is obtained from 11.5 g of 2-aminoheptane, 10.7 g of 3-pyridylcarboxaldehyde and 10, 0 g thiolactic acid. Product weight 14 g.
    NMR spectrogram (CDCEj) (delta) 1.2 (go, CHjCH-CCH J CH),
    / N. 4.0 (t, M-S-MF), 5.6 ni,
     H V) 8
    t, i, t88 (t, jQl
    7.6 M I /
    Elemental analysis data. 0 Found: C 65.49 H, 8.18, N 9.32.
    WITH
    Calculated,%: C 65.72; H 8.27,. N 9.58. 5 Example 34. 3H-Hexyl-5-methyl-2- (3-pyridyl) -4-thiazolidinone. Melting point is approximately 67-68s. From 10.1 g of P, α-hexylamine, 10.7 g of Q 3-pyridylcarboxaldehyde and 10.6 g of thiolactic acid are obtained. Product weight 5.7 g
    Elemental analysis data. Found,%: C-64.61; H 7.77; N 10.05 g
    C | 5-H2dM208 Calculated,%: C 64.71, H 7.97; And 10.05.
    Example 35. H- (3-Fluorophenyl) -5-methyl-2- (3-pyridyl) -4-tyazolidide non.
    The melting point is approximately 105 ° C; it is prepared from 11 g of 2-fluoroaniline, 10.7 g of 3-pyridylcarbonic aldehyde and 10.6 g of thio5 lactic acid. Product weight 16 g. Elemental analysis data. Found,%; C, 62.26; H 4.52; N 9.64.
    0 Calculated: C 62, H 4.54; N 9.72. .
    Example 36. 3- {4-Fluorophenyl) -5-methyl-2- {3-pyridyl) -4-thiazolidinone.
    5 Melting point is approximately obtained from 22.2 g of 4-fluoroaniline, 21.4 g of 3-pyridylcarboxaldehyde and 24 g of thiolactic acid. Product weight 36
    Elemental analysis data.
    Found,%: C 62.56; H 4.31; N 9.41.
    C, 5 H | .jFf "2 OS
    Calculated,%: C, 62.48; H 4, 54; N 9.72.
    5 Example 37. 3- (3-Nitrophenyl} -2- (3-pyridyl) -4-thiazolidinone.
    The melting point is 114-115 s, prepared from 13.8 g of 3-nitroaniline, 11 g of 3-pyridyl carboxaldehyde and 9 g of thioglycolic acid. Product weight 1.5 g
    Elemental analysis data.
    Found: C 55.74} H 3.69; N 13.77.  5 С, Calculated,%: С 55.81; H 3.65; N 13.95, Example 38.  3- (4-phenoxyphenyl) -2- (3-pyridyl) -4-thiaz-lidine The melting point was approximately 1–8–170 s, from 227 g of 4-phenoxyaniline, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid.  Product weight is 26 g.  Elemental analysis data.  Found,%: C 68.80 H 4.60 W 7.91.  C-zoH N tS Calculated;%: C 68.94, H 4.63, N 8.04.  Example 39  (2-Cyclo pentyl-1-methyl) J-ztil-5-methyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point was approximately 102 ° C, from 26 g of alpha-methylcyclopentane-ethylamine, 22 g of 3-pyridylcarboxalide guide, and 25 g of etylic acid.  Product weight 2 g.  NMR spectrogram (CDCr) (affairs ta) H2a, -CH5 /), 1.5 (I, -C-CH, - / P -IIZ HH 4, O ((J-C (O /), 5.6 (five-.  - C – N),.    Example 40  5-methyl-3- (alpha-methylbenzyl) -2- (3-pyridyl-4-thiazolidinone.  The melting point was approximately 890s, prepared from 12 g of alpha-methylbenzylamine, 10.7 C-pyridylcarboxaldehyde and 10.7 thiolactic acid.  Product weight 1.8 g  Elemental analysis data Found,%: C 68.17; H 5.87; N 9.31.  CnHigN OS Calculated,%: C 68.43; H 6.08; N 9.39. .  PRI me R 41.  3-Isopropyl-5-methyl-2- (3-pyridyl) -4-thiazolidine. The melting point was approximately 110-111 0, from 11.8 g of isopropylamine, 20.0 g of 3-pyridylcarboxaldehyde and 22.0 thiolactic acid.  Product weight 21 g.  Elemental analysis data.  Found,%: C 60.76 H, 6.54; N 12.07.  C, 7H | f, N20S Calculated,%: C 60.99; H 6.82; N 11.85.  Example 42  3- (3,3-Xylyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 140-142 s.  Prepared from 25 g of 3,5-dimethylaniline, 22 g of 3-pyridylcarboxaldehyde and 12 g of thiolactic acid.  Product weight 12 g.  NMR spectrogram (MSRC) (delta), 1.7 (q, methyl), 2.2 (s.  H11), 4, l (,), 6, l / S,), xCHdc 6.8-8.4 (t, -O) 8.8St, D JL).  -stg WT-T CHj “Elemental analysis data.  Found,%: C 68,17; H 5.83 N 9.31.  C. HigKjOS Calculated,%: C 68.43; H 6.08, Calculated, h N 9.39.  Example 43  2- (3-Pyridyl) - (2-thiazolyl) -4-thiazolidinone.  The melting point is approximately 6464-165 ° C, from 14.0 g of 2-aminothiazole, 15.0 g of 3-pyridylcarboxaldehyde and 13.0 g of thioglycolic acid.  Product weight 2.0 g.  Elemental analysis data.  Found,%: C 50.37; H 3.51, N 15.88.  C 1C: Calculated,%: C 50.17, H 3.44; N 15.96.  Example 44  3- {3,4-Ksilyl) -5-methyl-2- (3-pyridyl) -4-thiazolidide. . non  The melting point is approximately 189s, from 12, 1 g of 3,4-dimethylaniline, 10.7 g of 3-pyridylcarboxaldehyde, and 12thytilaminoic acid.  Product weight 16 g.  NMR spectrogram (dimethyl sulfoxide) (delta) 2.6 (d, methyl).  H 2.1 (S, methyl), 4.2 (a, -C-), CxI-t 6. 4S, -fx), 8 ,,) Elemental analysis data.  Found,%: C 68.64, H 6.22, N 9.29.  C (T IgNgOS Calculated,%: C 68.43-, H 6.08 / N 9.39.  Example 45, (1-Label of sipropyl) - (2- (3-pyridyl) -5-methyl-4-thiazolidinone.  Melting point was approximately -112 ° C, and 8.9 g of 2-amino-1-methoxypropane, 10.7 g, are also obtained. 3-pyridylcarboxaldehyde and 15 g of thiolactic acid.  Product weight 6.9 g  NMR (CDCt-j) (del) 1.3 (s, methyl) 3.3 (S, oxyH, n), 3.8f. f-C (0) j5 ,. 8 (S, -C СНзS7, e (. , "| ). c, e (“, jQL) Example 46.  3-Iopropyl-2- (3-pi dil) - 4-thiaeolidinone.  The melting point was approximately 119-120 ° C, from 7 g of isopropylamine, 15 g of 3-pyridylcarboxaldehyde, and 13 g of thiogric acid.  Product weight 12 Elemental analysis data. .  Found,%: C 59.19} H 6.25, N 12.32.   .  Sc H, 4N20S Calculated,%: C 59.43J H 6.35; N 12, 60  Example 47  3- {Cyclohexy methyl) -5-methyl-2- {3-pyridyl) -4t-thiazolidine.  Melting point: 73-74 °, prepared from 10.7 g. 3-pyr dilcarboxeldehyde ,.  11.3 g cycle of hexanmethanamine and 10.8 thiolactic acid.  Product weight 41 g. .  .  Elemental analysis data.  Found,% C 65.91 / H 7.47; N 9.69.  .   Calculated,%: C, 66.17; H 7.64; N 9.6. five.  Example 48  3-Cyclooctyl-5-methyl-2- (3-pyridyl) -4-thiazolvd non.  Melting point was approximately 58-61 ° C, prepared from 12.7 g of cyclooctylamine, 1. 0.7 g of 3-pyridylcarboxaldehyde and 10.6 thiolactic acid.  Product weight 11.2 g  Elemental analysis data.  Found,%: C, 66.89; H, 7.72 / N; 9.58.  C 11 H24N20S Calculated,%: C 67.07, H 7.95, N 9.20.  Example 49  5-Methyl-3-phenyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 159-161 ° C, prepared from 10.6 g of aniline, 21.4 g of 3-pyridylcarboxaldehyde and 21.2 g of thiolactic acid.  Product weight 15 g.   .  Element data.  from the analysis.  Found,%: C 66.59 / H 5.07; N 1-0,59.  C | 5-NtsK203 Calculated,%: C 66.64; H 5.22; N 10.36.  11 p and me p 50.  5-Methyl-3 (2-tolyl) -2- (3-pyridyl) -4-thiazolidinone.  In the form of an oil-like product, 21.4 g of 2-toluidine, 21.4 g of 3-pyridylcarboxaldehyde and 25 g of thiol milk acid are obtained.  Product weight 6 g, NMR spectrogram (CDCfj) (delta) 1.6 (q, methyl), 2.1) 1 (), (B, methyl), CH3 HH 5, b (5,), 7.1Gt . ) jQi. -).  N N Elemental analysis data.  Found,%: C 67.54, H 5.57, N 10.02.  Calculated,%: C 67.58, H 5.67; N 9, 89  Example 51  5-Methyl-3- - (4-methyLthiophenyl) -2- (3-pyridyl) -4-thiazolidinone.  Melting point is approximately 147-148s, from 17.5 g of 4-methylthioaniline hydrochloride, 10.7 g of 3-pyridylcarboxaldehyde and 12 g of thiolactic acid.  Product weight 23 g.  Elemental analysis data.  Found,%: C 60.63 H 4.90; N 9.00.  C, H, 6N20S: Calculated,%: C 60.73; H 5.10; N 8,85.  Example 52  5-Methyl-3- 2- 1-methoxypro 2 L) -2- (3-pyridyl) -4-thiaeolidinone.  The melting point is approximately 111-112 ° C., prepared from 8.9 g of 2-amino-1-methoxypropane, 10.7 g of 3-pyridylcarboxaldehyde and 15 g of thiolactic acid.  Product weight 2.1 g  The product was identified by NMR spectrogram data.   Example 53  3- (4-nitrophenyl) -2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 142-14 ° C, prepared from 18.8 g of 4-nitroaniline, 11 g of 3-pyridylcarboxaldehyde and 9 g of thioglycolic acid.  Product weight 4.0 g.  Elemental analysis data.  Found,%: C 55.66, H 3.61; N 13.62.  C 14 h, C 55.8.1, H 3.68; Calculated,%:, N 13.95.  Example 54  2- (3-pyridyl) -3- (2-coronyl) -4-thiazolidinone.  The melting point is approximately 143 ° C, obtained from.  14 g of carborninamine, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid.  Product weight 7.5 g  Elemental analysis data.  Found,%: C 65.39, H 6.40; N 10.05.  .  C 65.66; H 6.6i; Calculated,%; 10.21.  55.  3- (2,4-difluoro) Example of phenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 102 s, prepared from 6 g of 2,4-difluoroaniline, 6 g of 3-pyridylcarboxaldehyde and 8 g of thiolactic acid.  Product weight 3.2 g.  Elemental analysis data.  Found,%: C 58.69, H 3.94; 8.84.    .  „F NjOS Calculated,%: C58,81; H 3.95, N 9.14.   and meper 56.  3- (4-Iodophenyl) -5-methyl-2- (3-pyridyl-4-thiazolidinone.  The melting point is approximately 149-150 ° C, from 21.9 g of 4-iodoaniline, 11 g of 3-pyridylcarboxaldehyde and 12 g of thiolactic acid.  Product weight 12 g.  Elemental analysis data.  Found,%. : C 45.24; H 3.09 N 6.97.  C ,, H INjOS C 45.47, H 3.31; Calculated,%: N 7.07.  57.  5-Methyl-3- {4-Example-methylbenzyl) -2-g- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately obtained from 12 g of 4-methylbenzylamine, 10.7 g of 3-pyridylcarboxaldehyde and 10.7 g, 5 of 4 NN pr and 1 and pr NN be-pr of 10 and pr N -N be. t on am de Ve (d about 4, N of molar acid.  Product weight 9 g  Elemental data analysis.  Found,%: С 68, Зз; H 5.79, 9.21.  С it Н I N lOS Calculated,%: С 68.48 Н 6.08, 9.39.  Example 58  5-Methyl-3-methylcyclohexyl) -2- (3-pyridyl) -thiazolidinone.  Melting point is approximately 108-109 ° C, to obtain 11.5 g of 4-methylcyclohexylamine, 5 g of 3-pyridylcarboxaldehyde 11 with thiolactic acid.  Product weight 500 mg.  Elemental analysis data.  Found,%: C 66.45, H 7.82; 9.78.  C, H, eN20S Calculated,%: C 66.17 H 7.64; 9.65.  Example 59  3- (2,4-Dichloroyl) -2- (3-pyridyl) -5-methyl-4 and azolidinone.  The melting point is approximately 125-12 bs to give 17.6 g of 2,4-dichlorobenzylamine, 7 g of 3-pyridylcarboxaldehyde, 12 g of thiolactic acid.  Product weight 15 g.  Elemental analysis data.  Found,%: C 54.38, H 3.71.8, 08 C | feH Calculated,%: C 54.40, H 3.99, 7.93.  Example 60  3- (2 -; - Methoxy-nzil) -5-methyl-2- (3-pyridyl) -4 iosolidinone.  In the form of an oil-like product, they are obtained from 13.7 g of 2-methoxy-1-benzyl, 10.5 g of 3-pyridyl-carboxalgide and 10.7 thiolactic acid.  since the product is 2 g.  NMR spectrogram (CDC t) elta) 1.7 (q, methyl) 3.7 (s, V simethyl), 4.1 SC 5 (h, methylene) 5.5 (5, - CI) e8 / rn, jQ, H 1 Data of elemental analysis Found,%: C 64.71J H 5.53; 8.97.  C ,, H. N , 0-S Calculated: С 64,94; H 5.77, 8.91.  PRI me R 61.  3- (2-Furfuryl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone, the melting point is approximately 74 ° C, from 19.4 g F. URFURYLAMINE, 22 g 3-pyridylcarbox-g aldehyde and 25 g thiolactic acid.  Product weight b g  Element data. analysis.  Found,%: C 60.91 / H 5.30, N 10.43.  Calculated,%: C 61.29; -H 5.14, N 10.21.  Example 62  5-Methyl-2 - "(3-pyridyl-3- (tetrahydro-2-furanylmethyl) -4-thiazolidinone.  . 15 The melting point is approximately 86-87 ° C. 10.1 g of tetrahydro-2-furanmethanamine and 10.7 g of thiolactic acid are obtained from 10.6 g W-pi idiylcarboxaldehyde, 20 Product weight 5.5 g  Elemental analysis data.  Found,%: C 60.15 J H 6.36; N 10.20.  C | 4H, gH202S25 calculated,%: C 60.41; H 6.52; S 10.06.  PRI me R 63.  3- (2-Dimeti / 1-aminoethyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone. 30 In the form of a solid, 10.7 g of 3-pyridylcarboxaldehydeDa, 8.8 g of 2-dimethylaminoethylamine and 12 g of thioglycolic acid are obtained.  Product weight 12 g.  NMR spectrogram (CDCC = delta), 1.6 ((5, methyl) 2.1 (, dimethylamine), 2.6 (m, methylene), 3.9 (w methylene) 5.9 (5. -C-) 7.6 (. , Yl | KjQL).  8.8 (fn ,, -N.  N N Elemental analysis data.  Found,%: C 58, H, 6.99) N, 15.53.   Calculated,%: C, 53.87; H, 7.17; H 15.85.  PRI mepera 64.  3-t (2,6-Dichlorophenyl) amino-5-methyl-2- (3-pyridyl) -4-thiazolidinone.  Melting point is approximately 198-200s, from 11 g of 3-pyridylcarboxaldehyde, 21.3 g of 2,6-dichlorophenylhydrazimhydrochloride and 7 g of thiolactic acid are obtained.  60 Product weight 2g.  Elemental analysis data.  Found,%: C 50.80, And 3.62, N 12.03.  C |, 5H |.   N 4, pr cha de.  on the pr of NK ti-tut are 22 24 dU ti -4 pr 24 3mo N N ta 4.  Calculated,%: C 50.86; H 8.70; 11.84.  PRI me R 65.  3- (3-chlorop-4-melfeni-l) amino-5-methyl-2- (3-pyridyl).  thiazolidinone.  The melting point is approximately 150-160 ° C, polished from 6.43 g of 3-pyridylcarboxalgide, 8.5 g of H-chloro-4-methylanilium and 6.7 g of thiolactic acid.  Product weight 10.5 g  Elemental analysis data.  Found,%: C 60.10, H 4.93; 8.76.  C, H, 5CfN20S Calculated,%: C 60.28; H 4.74; 8.79.  Example 66  3- (2,4-Dimelphenyl) -5-methyl-2- (3-pyridyl) -4iazolidinone.  Melting point was about 121-123 ° C, from 25 g of 2,4-dimethylaniline, g of 3-pyridylcarboxaldehyde and g of thiolactic acid.  Weight 14 years  YAG1R spectrogram (COCC-j) (del) 1.7 (d methyl, 2.2 ((3 methyl), H P m and m p 67.  3- (2-Trifluormelphenyl) -5-methyl-2- (3-pyridyl) -thiazolidinone.  The melting point is approximately obtained from g of 2-trifluoromethylaniline, 16, g of pyridylcarboxaldehyde and 18 g of thiolic acid.  Product weight 4.0 g.  The data of elemental analysis, Found,%: C 53.64 H 4.22; 8.02.  CjjHigHjFjOS Calculated,%: C 53.98, H 4.24 / 7.86.  NMR spectrogram (USSR,) (del / H) 1.8L S-C- (J {0) CHa H / «| t, -C-.  .  -6. 0 And l, i6 EXAMPLE 68.  3- {4-bromo-3-methi-phenyl) -5-methyl-2- (3-pyridyl) -4-thiae lidinone.  Melting point is approximately 127-129 ° C, prepared from 11.2 g of 4-bromo-3-methylaniline, 6.4 g of 3-pyridylcarboxaldehyde and 6.7 thiolactic acid.  Product weight 12.2 g  Elemental analysis data.  Found,%: C 51.64-, H 4.22; N 7.82.  C, N VgM205 Calculated,%: C 51.44, H 4.03 N 8.00.  PRI me R 69.  3- (4-Chlorophenyl) -5, 5-dimethyl-2- (3-pyridyl) -4-thiazolidinone.  In 150 ml of anhydrous tetrahydrofuran, cooled to, in a dry nitrogen atmosphere, 25 m of hexane solution of L-butyllithium is added, the latter being added in one portion.  The mixture is cooled again to -7 ° C and a solution of 15 g of (3- (4-chlorophenyl) 5-methyl-2- {3-pyridyl) -4-thiazy lidinone (prepared as described above in Example 1 in 100 ml of anhydrous tetrahydrofuran.  After a further 0.5 h after completion of the addition to the same mixture, 14 g of methyl iodide are added dropwise, continuing the stirring, after which the reaction mixture is stirred overnight, and then the mixture is allowed to gradually warm to room temperature.  The reaction is carried out by adding water and extraction treatment with diethyl ether. The ether layer is dried over anhydrous magnesium sulphate, agent. The mixture is filtered and the filtrate is concentrated in vacuo to give a residual oil. This butter-like product is crystallized using a mixture of petroleum ether (c. kip  60-70C) with diethyl ether.  Thus, a product is obtained which has a melting point of approximately 140-141 ° C, which is identified as 3- (4-chlorophenyl) -5,5-dimethyl-2- (3-iridyl) -4-thiazolidinone.  Product weight 4.8 g  NMR spectrogram (CDCE) (DMSO (delta), 1.7 (S, methyl), 6.3 (s, -c - KV 7.2 (S, - (j-ci),.     Elemental analysis data.  Found,%: C 60.07; H 4.67-, N8.52.  . CtNjOS Calculated,%: C 60.28; H 4.74; N 8.79.  Analogously to Example 69, the following compounds are prepared.  PRI me R 70.  5-Butyl-3- (4-chlorophenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 76-77 ° C, prepared from 15 g of 3- (4-chlorophenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone, 25 ml of It-butyl lithium hexane solution and 9 g of N butylidene .  Product weight 2 g. Elemental analysis data.  Found,%: C 63.03} H 5.66; N 8.03.  C, pH, Calculated, -%: C 63.23; H 5.37, N 7.76.  PRI me R 71.  3- (4-Chlorfennl) -5-methyl-3-propyl-2-1 (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 81-83 ° C, prepared from 15.2 g of 3- (4-chlorophenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone (prepared as in Example 1), 8.5 g of R - propyl iodide and 23 hexane solution P.  butyl lithium  Product weight 1.6 g  Data of elemental analysis.  Found,%: C 62.55; H 5.28, N 8.13.  C, H-ClN-Oe Calculated,%: C 62.39; H 5.52; N 8.08.  Example 72  3- (4-Chlorophenyl) -5-hexyl-5-methyl-2- (3-pyridyl) -4-thiazolidinone.  The melting point is approximately 82-83 0, prepared from 15.2 g of 3- (4-chlorophenyl) -5-methyl-2- (3-pyridyl) -4-thiazolidinone prepared analogously to example 1, 10.5 g of U - hexyl iodide and 23 ml of 1-butyl lithium hexane solution.  Product weight 1.5 g  Elemental analysis data.  Found,%: C 64.59; H 6.23; N 7.19.  C. -H-JZlNj-OS Calculated,%: C 64.85; H 6.48, N 7.20.  PRI me R 73.  5-Butyl-3- (4-chlorophenyl) -2- (3-pyridyl) -thiazolidinone.  The melting temperature is about 93-94 seconds.  9.2 g of H-butyl iodide and 25 ml of a hexane solution of IV-butyl lithium are obtained from (4-chlorophenyl) -2- (3-pyridyl) -4-thiazolidinone.  Product weight 700 mg.  Elemental analysis data.  Found,%: C 62.11, H 5.28, N 8.08.   Calculated,%: C, 62.3; H, 5.52; N 9-, 08.  PRI me R 74.  3- (2-Methoxyphenyl) -2- (3-pyridyl) -4-thiazolidino This compound is prepared in the form provided.  Stage 1.  A mixture of 17 g of O-anisidine, 15 g of 3-pyridylcarboxaldehyde and 13 g of thioglycolic acid in toluene is boiled for several hours.  The mixture obtained as a cancer product is cooled, and the precipitated precipitate is collected on a filter.  The melting point of the product obtained in an amount of 20 g is approximately 118-120 s. It was identified by NMR and IR spectrograms as 0-methoxyaniline - (3-pyridyl-methyl) -thio acetic acid.  Stage 2.  A mixture of 5 g of (o-methoxyaniline) - (3-pyridyl) -methyl) thio-acetic acid, 3.4 g of dicyclohexylcarbodiimide and 300 ml of toluene is boiled for several hours. Then the toluene is removed in vacuo.  The residue thus obtained was chromatographed on a column of silica gel {toluene, and elution was carried out with a mixture of acetone x; toluene  The target fraction is concentrated, and the residue is recrystallized from a mixture of diethyl ether and pentane to obtain a product, the melting point of which is approximately 104-105 ° C and. which was identified as 3- (2-methoxyphenyl) -2- (3-pyridyl) -4-thiazolylinone.  Product weight 1.5 g, Elemental analysis data.  Found,%: C 61.47; H 4.86; N 9.97.   Calculated,%: C, 61.29; H, 5.14; N, 10.21.  PRI me R 75.  5-Methyl-2- (3-pyridyl) -3- (3-trifluoromethylthiophenyl) -4-thia-oolidinone.  This compound is prepared in a stepwise process.  Stage 1.  A mixture of 15 g of triflesmethylthio-3-nitrubenzene in 100 ml of absoluted methanol is subjected to hydrogenation in the presence of a skeletal nickel catalyst using a Parr hydrogenation apparatus.  After the absorption of hydrogen ceases, the reaction is stopped, the catalyst is filtered off and the filtrate is concentrated to give a product weighing 12 g, which has been identified as trifluoromethylthio-3-aminobenzene.  Stage 2.  A mixture of 11 g of trifluoromethylthio-3-aminobenzene, 7, T g of 3-pyridyl-carboxaldehyde in 200 ivui of toluene is boiled for 2 hours with the use of a DinaStark trap, which collects the water released during the course of the reaction.  A total of 1.2 ml of water was thus isolated.  The mixture obtained as a reaction product is cooled and concentrated in vacuo.  The residual oil is dissolved in toluene and chromatographed on a silica gel column.  The field material was eluted using, as eluent, a 5% solution of acetone in toluene, with several fractions from the column being tested for composition by thin layer chromatography.  Then the appropriate fractions are collected and concentrated to give an oil-like residue.  The isolated material, which is a yellow oil-like product, in an amount of 15 g, according to NMR spectrogram data, is identified as 3- (3-trifluoromethylthio) - (3-pyridylmethylene) -benzenamine.  The same material without prior purification is then used in the next stage of the process.  Stage 3.  A mixture of 14 g of 3- (3-trifluoroMethylthio) - (3-pyridyl ethylene) -benzenamine, 8 g of thiolactic acid and 200 ml of toluene is boiled for about 6 4, d using a Dean-Stark trap into which water is collected, secretions c as a result of the reaction.  The mixture obtained as a cancer product was concentrated in vacuo, and the residue thus obtained was dissolved in toluene and subjected to chromatography on a silica gel column.  The product is eluted from the column using a 5% acetone solution in toluene, and the combined fractions are concentrated to give a yellow oil-like product in an amount of 6 g.  It is identified as 5-methyl-2- (3-pyridyl) -3- (3-trifluoromethylthiophenyl) -4-thiazolidinone.  PRI me R 76. .  3- (4-Chlorophenyl) -2- (3-pyridyl) -3-pyr-4-thiazalinone hydrochloride.  A solution of 1.5 g of 3- (4-chlorophenyl) -2- (3-pyridyl) -4-thiazalidinone is prepared analogously to example 19 in diethyl ether, which is then cooled and saturated with anhydrous hydrogen chloride.  The precipitated solid material was filtered and identified as 3- (4-chlorophenyl) -2- (3-pyridyl) -4-thiazolidinone hydrochloride. .  Example 77.  3- (5-Chlorophenyl) -5- (methylthio) -2- (3-pyridyl) -4-thiazolidinone.
    Example 78. 3- (4-Chlorophenyl) -5, 5-bchc - (methylthio) -2- {3-pyridyl) -4-thiazolylindonone.
    A mixture of 10/1 g of diiopropylamine with 500 ml of tetrahydrofuran is cooled to a temperature of approximately 0 ° C in a nitrogen atmosphere. It is added dropwise to it and with stirring 45 ml of a hexane solution of the h-butylity and stirring is continued for approximately 30 minutes. After this addition is complete, the mixture is cooled to about a temperature and a solution of 14.5 g of 3- (4-chlorophenyl) -2- (3-pyridyl) -4-thiazodidinone (analogously to example 19) in 100 ml is added dropwise to it. tetrahydrofuran. After 30 minutes after completion of this operation, 9.4 g of methyl disulfide is added to the mixture. The remaining reaction mixture is stirred overnight and then allowed to gradually warm to room temperature. The reaction mixture is treated by adding dropwise water at room temperature. Next, the organic phase is subjected to extractive treatment with methylene chloride. The methylene chloride layer is washed with a dilute aqueous solution of hydrochloric acid. The methylene chloride layer is separated and dried over anhydrous sodium sulfate. The drying agent is filtered off and the filtrate is concentrated under vacuum.
    with obtaining residual butter-like product. This oil-like product is dissolved in toluene and chromatographed on silica gel. The elution is carried out with a 10% solution of acetone in toluene, and the separation is carried out in such a way that, after concentrating the fractions, a product is obtained, the melting point of which is approximately 104–10 ° C and a weight of 1 g, which is identified as 3- (4- hlrrphenyl) -5- (methylthio) -2 (3-pyridyl) -4-tizolidinone.
    Elemental analysis data.
    Found,%: C 53.40; H 3,, 91; N 8.20.
    C (5H ,, CtN OB,
    Calculated% i, 48, H 9.89; N 8.32.
    The second product, the melting point of which is approximately 132-133 ° C and the weight is 400 mg, is isolated in exactly this way and identified as 3- (4-chlorophenyl) -5, 5-5is- (methylthio) -2- (3- pyridyl) -4-thiazolidinone.
    Elemental analysis data.
    Found,%: C 50.09 / H 3.91; 7.08.
    ,
    Calculated,%: C 50.18; H 3.95; 7.32.
    权利要求:
    Claims (2)
    [1]
    1. METHOD FOR PRODUCING 4-THIAZOLIDINE COMPOUNDS of the general formula
    H C — TT-R. 1 and 1 $ 2О0
    I where R | - C -Cq-alkyl, C ^ -Cg-cycloalkyl, metal, phenyl, halogen phenyl trifluoromethyl phenyl, methoxybenzyl, methylbenzyl, halogenbenzyl, dimethylaminoethyl, methylcyclohexyl, cyclohexylmethyl, 1- (2-cyclopentyl-1-methyl) ethyl, ot> 2-T | thinned, nitrophenyl, phenoxyphenyl, (tetrahydro-2-furanyl) methyl, trifluoromethylthiophenyl, 4-methylthiophenyl, 2-norbornyl, furfuryl, 2- (1-methoxy) propyl, methoxyphenyl, tetrafluoroethoxybenzyl, xylyl, tolyl, halotolyl, halophenylamino or
    3,4- (methylenedioxy) benzyl;
    R £ - hydrogen, C- Cb- alkyl or methylthio radical)
    Rj is hydrogen, methyl or methylthio radical, characterized in that 3-pyridylcarbaldehyde is reacted with a substituted amine of the general formula r 1 -nh 2 , where R has the indicated meanings, followed by reaction of the obtained product with thioglycolic or thiolactic acid or the target product where Rg is hydrogen and
    R.J-methyl, is transferred by alkylation to the target product, where R C ^ -Calkyl, or the target product, where and is hydrogen, are transferred to the target product, where R and / or R-j is methylthio radical.
    [2]
    2. The method according to claim 1, characterized in that when R {-NH 2 is a spatially hindered amine, the process is conducted in the presence of a cyclizing agent.
    »S.U w) 10791 75
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    同族专利:
    公开号 | 公开日
    CH643842A5|1984-06-29|
    RO82467A|1983-09-26|
    RO82467B|1983-08-30|
    GB2031892A|1980-04-30|
    EP0010420A1|1980-04-30|
    HU185844B|1985-04-28|
    IE48966B1|1985-06-26|
    DD146539A5|1981-02-18|
    RO78232A|1982-02-01|
    DK434779A|1980-04-17|
    AU5165479A|1980-04-24|
    LU81779A1|1980-01-24|
    PH15765A|1983-03-24|
    PT70313A|1979-11-01|
    ES485073A1|1980-10-01|
    AR225154A1|1982-02-26|
    BR7906634A|1980-07-08|
    NZ191818A|1982-05-25|
    FR2439197B1|1986-04-25|
    JPS5555184A|1980-04-22|
    CS216535B2|1982-11-26|
    DD150747A5|1981-09-16|
    DE2967188D1|1984-09-27|
    ES8200105A1|1980-12-01|
    PL218994A1|1980-07-01|
    GB2031892B|1983-08-17|
    PL127226B1|1983-10-31|
    EP0010420B1|1984-08-22|
    RO78231A|1982-02-01|
    ZA795488B|1981-05-27|
    ATA670079A|1983-05-15|
    DD150746A5|1981-09-16|
    GR71652B|1983-06-20|
    FI793191A|1980-04-17|
    HU187550B|1986-01-28|
    IE791949L|1980-04-16|
    RO82359B|1983-07-30|
    PL125628B1|1983-06-30|
    BE879368A|1980-04-14|
    IL58446A|1983-10-31|
    ES485072A0|1980-12-01|
    RO82359A|1983-08-03|
    PT70314A|1979-11-01|
    FR2439197A1|1980-05-16|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US95170878A| true| 1978-10-16|1978-10-16|
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