Syntheses of some Alkyl, Cycloalkyl and AryI2-Aminophenyl Sulfones
SummarySyntheses of the alkyl, cycloalkyl and aryl 2-aminophenyl sulfones 10 were achieved by oxidation of the corresponding 2-nitrophenyl sulfides 7 to the 2-nitrophenyl sulfones 9 followed by ethanolic BPchamp-reduction. The sulfides 7 in turn were obtained either by reactions of 2-nitro-thiophenol (8) with the appropriate alkyl and cycloalkyl halides or of 2-chloro-nitrobenzene (5) with the relevant thiols. Condensation of 2-nitrobenzenesulfinic acid (3) with bromoacetic acid in aqueous alkaline solution led -presumably via 2-nitrophenylsulfonylacetic acid (4) -to methyl 2 nitrophenyl sulfone (l), reduction of which gave 2-aminophenyl methyl sulfone (2). Treatment of 2-aminothiophenol (11) with t-butyl alcohol in aqueous sulfuric acid gave 2-aminophenyl t-butyl sulfide (12), which was acetylated to o-t-butylthio-acetanilide (13). Oxidation of the latter to o-t-butylsulfonylacetanilide (14) followed by hydrolysis led to 2-aminophenyl t-butyl sulfone (15).
Als Methode zur Herstellung von
Alkylierung des Nitrothiophenols (I) mit den Halogeniden (II) bzw. des Nitrochlorbenzols (VI) mit den Thiolen (VII) gibt die Nitrophenylsulfide (III) bzw. (VIII), deren Sulfone (IV) bzw. (IX) nach Be/champ zu den 2‐Amino‐phenyl‐sulfonen (V) bzw. (X) reduziert werden.
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