Notizen zur Synthese von 2‐Aminophenylsulfonen

<jats:p><jats:bold>Syntheses of some Alkyl, Cycloalkyl and Aryl 2‐Aminophenyl Sulfones</jats:bold></jats:p><jats:p>Syntheses of the alkyl, cycloalkyl and aryl 2‐aminophenyl sulfones <jats:bold>10</jats:bold> were achieved by oxidation of the corresponding 2‐nitrophenyl sulfides <jats:bold>7</jats:bold> to the 2‐nitrophenyl sulfones <jats:bold>9</jats:bold> followed by ethanolic <jats:italic>Béchamp</jats:italic>‐reduction. The sulfides <jats:bold>7</jats:bold> in turn were obtained either by reactions of 2‐nitro‐thiophenol (<jats:bold>8</jats:bold>) with the appropriate alkyl and cycloalkyl halides or of 2‐chloro‐nitrobenzene (<jats:bold>5</jats:bold>) with the relevant thiols. Condensation of 2‐nitrobenzenesulfinic acid (<jats:bold>3</jats:bold>) with bromoacetic acid in aqueous alkaline solution led ‐ presumably <jats:italic>via</jats:italic> 2‐nitrophenylsulfonylacetic acid (<jats:bold>4</jats:bold>) ‐ to methyl 2 nitrophenyl sulfone (<jats:bold>1</jats:bold>), reduction of which gave 2‐aminophenyl methyl sulfone (<jats:bold>2</jats:bold>). Treatment of 2‐aminothiophenol (<jats:bold>11</jats:bold>) with <jats:italic>t</jats:italic>‐butyl alcohol in aqueous sulfuric acid gave 2‐aminophenyl <jats:italic>t</jats:italic>‐butyl sulfide (<jats:bold>12</jats:bold>), which was acetylated to <jats:italic>o</jats:italic>‐<jats:italic>t</jats:italic>‐butylthio‐acetanilide (<jats:bold>13</jats:bold>). Oxidation of the latter to <jats:italic>o</jats:italic>‐<jats:italic>t</jats:italic>‐butylsulfonyl‐acetanilide (<jats:bold>14</jats:bold>) followed by hydrolysis led to 2‐aminophenyl <jats:italic>t</jats:italic>‐butyl sulfone (<jats:bold>15</jats:bold>).</jats:p>