Process for the preparation of 2-(2-halogenoethylthio)-phenylsulfonamides
    1.
    发明授权
    Process for the preparation of 2-(2-halogenoethylthio)-phenylsulfonamides 失效
    制备2-(2-甲基乙酰氧基)苯基磺酰胺的方法

    公开(公告)号:US5166430A

    公开(公告)日:1992-11-24

    申请号:US585743

    申请日:1990-09-20

    CPC分类号: C07D521/00 C07C323/67

    摘要: A 2-(2-halogenoethylthio)-phenylsulfonamide of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine, is prepared by a process wherein:a) a 2-halogenophenylsulfonamide of the formula II ##STR2## in which X is fluorine, chlorine or bromine, is converted, in the presence of a base, together with a mercaptan of the formula IIIR-SH (III) in which R is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkyl substituted by phenyl, into a 2-sulfenylphenylsulfonamide,b) this compound is oxidized to give the 2-sulfinylphenylsulfonamide,c) the resulting 2-sulfinylphenylsulfonamide is converted, in the presence of an acid, into the disulfide of the formula VI ##STR3## d) the disulfide of the formula VI is reduced to the 2-mercaptophenylsulfonamide,e) this compound is then converted, by means of a trialkylamine of the formula X(R.sub.1).sub.3 N (X) in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, into the 2-mercaptophenylsulfonamide trialkylamine salt, andf) this compound is then reacted with a halogenofluoroethane of the formula IXY-CH.sub.2 CFZ.sub.1 Z.sub.2 (IX) in which Y is chlorine or bromine and Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine.

    摘要翻译: 其中Z 1和Z 2彼此独立地为氢,氟或氯的式I(I)的2-(2-卤代乙硫基) - 苯基磺酰胺是通过以下方法制备的,其中:a)将2-卤代苯基磺酰胺 其中X是氟,氯或溴的式II(II)在碱的存在下与式III的硫醇R-SH(III)一起转化,其中R是C 1 -C 6烷基 或被苯基取代的C1-C6烷基取代成2-亚磺酰基苯基磺酰胺,b)将该化合物氧化得到2-亚磺酰基苯基磺酰胺,c)将所得的2-亚磺酰基苯基磺酰胺在酸存在下转化成式 (VI)d)将式VI的二硫化物还原成2-巯基苯基磺酰胺,e)然后通过式X(R1)3N(X)的三烷基胺将该化合物转化为其中R1 是C 1 -C 4烷基,进入2-巯基苯基磺酰胺三烷基胺盐,f)然后使该化合物反应 其中Y为氯或溴,Z 1和Z 2彼此独立地为氢,氟或氯,式IXY-CH2CFZ1Z2(IX)的卤代氟代乙烷。