• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Verfahren zur Herstellung von 4,4'-Bis-benz-ox(-thi, -imid)-azol-2-yl-stilbenen der Formel worin R, R1, R2 und R3 gleich oder verschieden sind und Wasserstoff, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl, Chlor, Brom, Nitro oder Sulfo und X Sauerstoff, Schwefel oder NH bedeuten, wobei man (4-Halomethyl)-imino- benzoesäurealkylester der Formel oder deren HCI oder HBr-Salze, wobei R C1-C4-Alkyl oder C1-C4-Alkoxyethyl und X Cl oder Br bedeutet, mit o-Aminophenol, o-Aminothiophenol oder o-Phenylendiamin umsetzt und die dabei erhaltenen 2-Benz-ox(-thi, -imid)-azolyl-4-halomethylbenzole mit einer etwa equivalenten Menge Natrium-tert.- butylat reagieren läßt. Die dabei erhaltenen Stilbenverbindungen dienen als optische Aufheller.
    公开号:SU1190986A3
    申请号:SU833585891
    申请日:1983-05-04
    公开日:1985-11-07
    发明作者:Хайсс Лоренц
    申请人:Хехст Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a process for the preparation of 4, A-bis-benzox- (thio, im-azol-2-yl-stilbenes of the general formulas are the same or different and represent a hydrogen atom, alkyl, Cj-C4-alkox carbonyl, chlorine atom of bromine, nitro or sulfo group, oxygen, sulfur or NH atom. The purpose of the invention is to reduce the consumption of sodium tert-butylate and expand the range of production of water stilbenes. Example 1. 110 g (0.5 mol) of P-chloromethyl-amino-benzoic acid methyl ester hydrochloride and 54 g (0.5 mol) o-aminophenol is dissolved in 800 ml of methanol and the solution is stirred for 1 at 65 C. Then it is cooled to room temperature, about 500 ml of water is added to a solution of ammonium chloride formed and the precipitate is filtered off. After washing the precipitate with water and drying, 110 g (90.5%: from theoretical yield) of benzoxazolyl are obtained. -2- (4-chloromethyl) -benzene, mp 150-15I C. Found: C, 69.0; H, 4.10; N, 5.7; Cl, 14.5. Calculated: C, 69 , 1, H 4.1; N 5.8; C1 14.6. In 150 ml of dimethylformamide is dispersed in a nitrogen atmosphere 3, .6 g of tert-butanol and 1.6 g of sodium hydride (80%) and the suspension is moved within 1 h, after which 9.8 g (0.04 g ol) benzoxazolyl-2- (4-chloromethyl) benzene and stirring was continued for another 6 hours at 20 ° C. The reaction mixture is then diluted with 100 ml of water and adjusted to pH 5-6 with hydrochloric acid. After settling, the precipitate is thoroughly washed with water and methanol and dried. The result is greenish crystals of 4,4-bis-benzoxazolyl-2-yl-stilbene. Yield 8.1 g (97.8%) -. Mp. 355-: 360 ° C (lit. З62с) Found:%: C 80.6; H 4.3jN 6.8. Calculated,%: C 81.1; H 4.3; N 6,8. Example2. 3.6 g of tert-butanol and 1.6 g of sodium hydride (80%) are dispersed under an atmosphere of nitrogen in 150 ml of tetramethyl urea and stirred for 1 hour, then 9.8 g (0, 04 mol) benzoxazolyl-2- (4-chloro methyl) -benzene and stirred for 1 hour at 20 C. Then the mixture is diluted with 100 ml of water and adjusted to pH 5-6 with hydrochloric acid. After suction, the precipitate is thoroughly washed with water and methanol and dried. Greenish crystals of 4,4-bis-benzoxazol-2-yl-stilbene are obtained with a yield of 8.1 g (97, -8%). Melting point 355-360 ° C. Found:%: 80.5; H 4.2; N 6,8. Calculated,%: C 81.8; H 4.3; N 6,8. A similar result is obtained if the reaction is carried out in dimethyl: tamide, dimethyl sulfone, 1,2-dimetok siztan or N-methylpyrrolidone. Similarly, get given in abl. 14-halogenation, from which then get listed in table 2 stilbene derivatives.
    Table 1
    About About 310 310 5.7 91 30669, 6 3.3 5.8
    Initial compound
    Continuation of table 2
    权利要求:
    Claims (2)
    [1]
    1. METHOD FOR PRODUCING 4,4'-BIS-BENZOX- (THIO, IMID) -AZOL-2-IL-STILBENES of the general formula where R, R ( - R 3 are the same or different and represent a hydrogen atom, C ^ -C ^ alkyl, CC 4 - alkoxycarbonyl, a chlorine, bromine atom, nitro or sulfo group;
    X is an oxygen, sulfur or NH atom, characterized in that, in order to reduce the consumption of sodium tert-butylate and expand the range of stilbene derivatives, an alkyl ester of (4-halogenmethyl) iminobenzoic acid of the general formula where R is C ^ -C ^ is alkyl or C ^ -C 4 alkoxyethyl;
    X is a chlorine or bromine atom, or its hydrochloric or hydrobromic salts interact with g respectively with substituted o-aminophenol, 0.-aminothiophenol or O-phenylenediamine, followed by the reaction obtained
    [2]
    2-6 benzene- (thio, imide) -azolyl-4-halogenomethylbenzene with an equivalent amount of sodium tert-butylate in the medium of dimethylformamide, tetramethylurea, dimethylacetamide, dimethyl sulfone, 1,2-dimethoxyethane or N-methylpyrrolidone.
    2. The method of pop. 1, characterized in that the sodium tert-butylate is obtained in situ from sodium hydride and butanol.
    1 1190986 2
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    引用文献:
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    US3260715A|1962-12-17|1966-07-12|Eastman Kodak Co|Fluorescent bis-benzoxazolyl stilbenes|
    CA967959A|1965-03-12|1975-05-20|Nathan N. Crounse|4,4'-bis stilbene|
    FR1498700A|1965-10-04|1968-01-10|
    CH484930A|1967-08-25|1970-01-31|Ciba Geigy|Process for the preparation of aryloxazoles|
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    JPH0477747B2|1984-06-15|1992-12-09|Fuji Photo Film Co Ltd|
    DE3503776A1|1985-02-05|1986-08-14|Basf Ag, 6700 Ludwigshafen|BIS ISOINDOL PIGMENTS AND THEIR USE|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19823216723|DE3216723A1|1982-05-05|1982-05-05|METHOD FOR PRODUCING 4,4'-BIS-BENZ-OX-AZOL-2-YL STILBENES|
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