Aniline → Benzenesulfonamide, 4-methyl-N-phenyl-

Participants

Reaction Steps

The title compound was synthesized by triturating aniline (0.5 g, 5.36 mmol), powdered sodium bicarbonate (0.9 g, 1.07 mmol) and powdered p-toluene sulfonyl chloride (1.02 g, 5.36 mmol) for 5 min at rt. The reaction mixture was stirred with water, filtered, washed with water and dried to give 16 (1.13 g, 84.9%). Product was purified by FCC by using eluent as in 15 to give 16 as white powder (0.9 g), mp-95-97° C. (lit32A 96° C.); IR(CHCl3) 3255, 1599, 1342, 1160, cm−1; 1H NMR (500 MHz, DMSOD6) δ 2.37 (s, 3H, CH3), 6.53 (br, 1H, NH), and 7.04-7.65 (m, 9H, aromatic). HRMS calcd 270.05592 (C13H13NO2S.Na+), found 270.05589.

Provenance & Evidence