2-Nitroaniline → Nitrobenzene2nnbismethylsulfonyl

Participants

Reaction Steps

To a cooled (0° C.) solution of 2-nitroaniline (1 g, 7.25 mmol) in dimethylformamide (DMF, 10 mL) was added sodium hydride (608 mg, 25 mmol). After addition was complete methanesulfonyl chloride (1.69 mL, 21.8 mmol) was added and the reaction was warmed to room temperature and stirred for 1 hour. The reaction was then diluted with water and the product extracted with ethyl acetate. The organic layer was concentrated and purified by chromatography to provide N-(methylsulfonyl)-N-(2-nitrophenyl)methanesulfonamide (1.5 g, 70% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 7.89 (m, 1H), 7.80 (m, 2H), 3.58 (s, 6H).

Provenance & Evidence