Method of preparing cyclohexane derivatives of their salts

专利摘要:
Compounds of the general formula <IMAGE> wherein R1 is lower alkyl, phenyl, substituted phenyl or benzyl, R2 is lower alkyl, R3 is lower alkyl or lower alkenyl, R4 is hydrogen or lower alkoxycarbonyl, X is straight or branched chain lower alkylene, and n is 0, 1 0r 2; and metal salts and ammonium salts of the compounds defined hereinabove. The compounds are useful as herbicides.
公开号:SU884567A3
申请号:SU792705001
申请日:1979-01-05
公开日:1981-11-23
发明作者:Иватаки Исао；Сибуя Масами；Исикава Хисао；Кавана Такаси
申请人:Ниппон Сода Компани Лимитед(Фирма)；
IPC主号:

专利说明:

where Rj has the indicated meanings, followed by isolation of the desired product in free form or as a salt. The process is carried out in an inert solvent, for example, acetone, ether, alcohol, benzene, tetrahydrofuran, chloroalkanes, acetonitrile, ethyl acetate, dioxane, toluene, xylene and dimethyl sulfoxide. The reaction temperature varies from -10 ° C to the boiling point of the solvent, preferably 10-60 0. Example 1, 2- (1-Ethoxy-aminobutylidene) -5- (2-ethylthiopropyl) -cyclohexane-1,3-dione, 5 , 7 g of 2-butyryl-5 (2-ethylthiopropyl) cyclohexane-1,3 dione is dissolved in 20 ml of ethanol. 1.4 g of ethoxyamine is added to this solution and the resulting solution is stirred at room temperature for 5 hours. the reaction solution was poured into ice-cold water and the mixture was poured with hydrochloric acid. The mixture is extracted with chloroform, the chloroform solution is washed with water, dried with anhydrous magnesium sulphate — and when chloroform is removed by distillation under reduced pressure, 4.5 g of the expected product is obtained as a colorless oily substance, 1.5229, Example 2, 2- ( 1-Allyloxy-butylidene) -5- (2-ethylsulfinylpropyl) -cycpohexane-2 ,, 6 g of 2-butyryl-5 (2-ethylsulfinylpropyl) -cyclohex (H-1,3-Dione) is dissolved in 30 ml of ethanol. solution. add 1.6 g of allyloxyamine and the resulting solution is stirred at room temperature for 15 hours. At the end of the reaction, the stock solution was treated as in Example 1 to obtain 4.8 g of the title compound as a colorless oily substance, 1.5343. Example 3 with 2- (1-Allyloxy-butylidene) -5- (2-methylthioethyl) cylohexan-1, 2.6 g of 2-butyryl-5- (2-methylthioethyl cyclohexane-1,3 dione are introduced into a reaction with 0.8 g of allyloxyamine at room temperature for 10 hours in 20 ml of ethanol. Upon completion of the reaction, the resulting solution is treated as in Example 1 to obtain 3 g of the title compound as a colorless oily substance, nU 1.5402, 74 Example 4, 2 (1-Ethoxyaminopropylidene) (4 -chlorophenyl) -thioethyl cyclohexane-1,. 1.6 g of 2-propionyl-5 G2 (4-chlorophenylthio) ethyl cyclohexane-1,8-dione are reacted with 0.8 g of ethoxyamine at room temperature for 16 h, in 60 ml of methanol. At the end of the reaction, the resulting solution is treated as in Example 1, with a half portion of the oily product. After purification of the oily product by column chromatography, 1 g of the title compound is obtained in the form of a colorless oily substance, t, mp. 42-43 C .. PRI mpe R 5. 2- (1-Ethoxy-aminopropylidene) (p-tolylthio) isopropyl-cyclohexane-1 ,, 1.3 g 2-propionyl-5-1 (p-tolylthio) - isopropyl cyclo {4-hexane-1,3 dione is reacted with 0.3 g of allyloxyamine at room temperature for 15 hours in a mixture of 10 ml of benzene and 3 MP of ethanol. At the end of the reaction, the resulting reaction solution is treated as in Example 1, to obtain 1 g of the desired compound, G, pl. 77.5-79 ° C, Example 6. Sodium salt of 2- (1-ethoxyaminopropylidene) (4-hl6rphenylthio) ethyl cyclohexan-1, 3 -dione. O, 63 g of sodium methoxide was dissolved in 50 ml of methanol, and 4.5 g of 2- (1-ethoxyaminopropylene) (4-chlorophenylthio) -ethyl cyclohexan-1, 3 Dioia, prepared in Example 4, was added to the resulting solution, after removing ethanol from the mixture by distillation with poni-. 4.7 g of slightly yellowish crystals of the target compound are obtained, mp. 128-130 ° C (decomposition) Example 7. Copper salt of 2- (1-ethoxyaminopropylene) (4-chlorophenylthio) ethyl cyclohexane-1,3 dione. 1.6 g of the sodium salt obtained in Example 6 is dissolved in 30 ml of water, and 10 ml of an aqueous solution of 0.5 g of copper sulfate is added dropwise to the resulting solution. After stirring the mixture at room temperature for 30 minutes, the crystals are separated and recrystallized from a mixture of acetone and water to obtain 1 g of the green powder of the target compound, m, mp, 122 ° C (decomposition). 58 Example 8. Monohydrated to tetrabutylammonium salt 2- (1-etho-siaminopropylidene) (- chlorophenyl thio) these cyclohexane-1,3 dione. 1.5 g of 2- (1-ethoxyaminopropylidene) (-chlorophenylthio) ethyl cyclohexane-1, 3 Dione obtained in example i is dissolved in 15 ml of methanol. 1 g of a 10% methanol solution of tetrabutylammonium hydroxide is added to the solution and then the methanol is removed by distillation under reduced pressure. The remaining oily product is dissolved in 50 ml of water, provided with activated charcoal and extracted with 50 ml of methylene chloride. After the solution was dried with anhydrous magnesium sulfate, methylene chloride was completely distilled off under reduced pressure. The remaining oily product was allowed to stand until crystals formed. which are recrystallized from a mixture of benzene and ligrbium to obtain 1.6 g of white crystals of the target compound, m.p. 80-82 C. Example 9. 2- (1-Allyloxy-aminobutythyliden) -5- (2-methylsulfonylethyl) -methoxycarbonylcyclohexan-1, 3.-Dione. 3.5 g of 2-butyryl-5 (2-methylsulfonylethyl) -methoxycarbonylcyclohexane-1, 3-dione are reacted with O, 9 g of allyloxyamine at room temperature for 5 hours in 20 ml of ethanol. After the completion of the reaction, the resulting reaction solution was worked up as in Example 1 to obtain 3.1 g of white crystals of the target compound, mp. 9b, 5 ° C. Physical constants of other compounds of general formula I are given in the table.
CHs
ъ НСНпсн
SNS
Hg C HgSOQ IfHCHlJ CIS, 9 CHj
Cj hjsch
H-C4H SCHCHq CH
HC, .H SCHCH | j CHj
80 - 82
II
n 1.5232 n 1.5291
n | o 1,5337
n 1,5135
P 1.5280
eight
Table continuation;
25. CHjSOnCjH iUflt
ABOUT
5 - 56

eleven
kO.
12 Continuation of the table
Na198-199 (dec.)
13
li
Table continuation
15
sixteen
88 (5b7 Continuation of t. L / (tsy
17
Compound
510) „“
RlS (0) tt-X- JR Rg R
Bk. Sya.rsch SC,} {
85.
18 - {Continuation of the table
Physical constants, melting point, C or t salt
njf 1,5790
n 1.5811

87
69 - 70
96 - 97
about cif hif
89
90, Ci-l {
91.
0
92. Ct-f
93. ce-ff scoH,
g.JJ
 II
91.
95. 96.
97.
CH,
 1.5811

 1.5732
and
Cfth
f (: Hg NiCH),
C-H
 QhCH, Vc ,, 3 СЯ, 93 - 95
128-130 (dec.)
Na
172-173 (dec.)
Ca
P
122 (dec.)
Cu
 N () - H, iO 80 - 82
 - 50
nineteen
884567
20 Continuation of the table

权利要求:
Claims (1)
[1]
Claim
The method of obtaining derivatives of cyclohexane of the General formula I t CNHORj 25
Hv eo where R ^ * lower alkyl, phenyl unsubstituted or substituted by halogen, lower alkyl or lower alkoxy, or benzyl; 35
R ^ is lower alkyl;
R ^ is lower alkyl or lower alkenyl;
R ^ is hydrogen or lower alkoxycarbonyl; 40
X is a straight or branched lower alkylene, η -0.1 or 2, or their salts, with a 10¼ and the second c ^ i in that the compound of general formula P 45 where R ^ RipRg.X and η have the indicated values are reacted with a compound of general formula III
R ₃ 0NH _lf where RjMMeeT specified values, followed by isolation of the target product in free form or in the form of salt.

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法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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JP5873877A|JPS5642589B2|1977-05-23|1977-05-23|

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JP11294577A|JPS578099B2|1977-09-20|1977-09-20|

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JP13676577A|JPS5647184B2|1977-11-16|1977-11-16|

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JP2240678A|JPS5642590B2|1978-02-28|1978-02-28|

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