Notizen zur Synthese von 2‐Aminophenylsulfonen

Syntheses of some Alkyl, Cycloalkyl and Aryl 2‐Aminophenyl Sulfones Syntheses 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 Béchamp‐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 (1), 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‐butylsulfonyl‐acetanilide (14) followed by hydrolysis led to 2‐aminophenyl t‐butyl sulfone (15).