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

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Aniline (1.86 g, 0.02 mol) was dissolved in methylene chloride under nitrogen and triethylamine (3.8 mL, 0.02 mol) was added. This solution wascooled in an ice bath and a solution of p-toluenesulfonyl chloride (3.8 g, 0.02 mol) was added dropwise via a syringe. After stirring this solution for 4 h at room temperature, TLC analysis (silica gel, 20% ethyl acetate/hexane) indicated completion of the reaction. The reaction mixturewas poured into ether and the precipitate filtered. The ether layer was washed with water, dried over MgSO4 and concentrated to yield an oilymaterial. This crude product was chromatographed on silica using 35% ethyl acetate and hexane to obtain a solid which was further recrystallized in methylene chloride/hexane; m.p. 104° C.; 1H NMR (CDCl3) δ2.36 (s, 3H), 7.07-7.25 (m, 8H), 7.67-7.69 (d, 2H).

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