Aniline → 3-bromo-N-phenylbenzenesulfonamide

Participants

Reaction Steps

3-Bromobenzenesulfonyl chloride (51a) (1.0 g, 3.9 mmol) was added to a mixture of aniline (0.47 g, 5.1 mmol) in acetonitrile (10 ml) and sodium carbonate (1.3 g, 12.3 mmol) in water (10 ml). The mixture was stirred at ambient temperature for 1 hour and the reaction product was extracted with ethyl acetate (30 ml). The extract was dried (Na2SO4) and solvents were removed under reduced pressure to give the title compound (1.15 g, 94%) as an oil wich solidified upon standing. M.p. 98-100° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.94-7.48 (5H, m, C6H5); 7.50-7.96 (4H, m, C6H4); 10.36 (1H, s, NH).

Provenance & Evidence