4-Toluenesulfonyl chloride → 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester

Participants

Reaction Steps

To a solution of methyl 2-aminobenzoate (50 g, 0.32 mol) in pyridine (250 mL) at 10-15° C., tosyl chloride (95 g, 0.5 mol) was added in portions. The reaction mixture was warmed to room temperature and allowed to stir for 2 h. The reaction mixture was poured on to ice and the precipitate filtered and washed with dilute hydrochloric acid (200 mL×2) followed by water (200 mL×2). The solid was dried under vacuo to afford methyl 2-(4-methylphenylsulfonamido)benzoate (100 g, 99%). 1H NMR: (400 MHz, DMDO-d6) δ: 10.41 (1H, s), 7.85 (1H, d, J=7.6 Hz), 7.69 (2H, d, J=8.0 Hz), 7.57 (1H, t, J=7.2 Hz), 7.45 (1H, d, J=8.0 Hz), 7.36 (2H, d, J=8.0 Hz), 7.18 (1H, t, J=7.6 Hz), 3.82 (3H, s), 2.25 (3H, s).

Provenance & Evidence