Process for the preparation of...

C - Chemistry – Metallurgy – 07 – C

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C07C 323/67 (2006.01) C07C 319/18 (2006.01) C07D 521/00 (2006.01)

Patent

CA 2026355

CA- PS/5-17770/1+2/= Process for the preparation of 2-(2-halogenoethylthio)-phenylsulfonamides Abstract A 2-(2-halogenoethylthio)-phenylsulfonamide of the formula I Image (I), in which Z1 and Z2 independently of one another are hydrogen, fluorine or chlorine, wherein a) a 2-halogenophenylsulfonamide of the formula II Image (II) in which X is fluorine, chlorine or bromine, is converted, in the presence of a base, together with a mercaptan of the formula III R-SH (III) in which R is C1-C6alkyl or C1-C6alkyl substituted by phenyl, into a 2-sulfenylphenylsulfonamide of the formula IV Image (IV) in which R is as defined under formula III, b) this compound is oxidized to give the 2-sulfinylphenylsulfonamide of the formula V Image (V) in which R is as defined under formula III, c) the resulting 2-sulfinylphenylsulfonamide of the formula V is converted, in the presence of an acid, into the disulfide of the formula VI Image (VI) d) the disulfide of the formula VI is reduced to the 2-mercaptophenylsulfonamide of the formula VII Image (VII) e) this compound is then converted, by means of a trialkylamine of the formula X (R1)3N (X) in which R1 is C1-C4alkyl, into the 2-mercaptophenylsulfonamide trialkylamine salt of the formula VIII Image (VIII) in which R1 is as defined under formula X, and f) this compound is then reacted with a halogenofluoroethane of the formula IX Y-CH2CFZ1Z2 (IX) in which Y is chlorine or bromine and Z1 and Z2 independently of one another arehydrogen, fluorine or chlorine.

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