Methyl p-toluenesulfonate → Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)

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Reaction Steps

A mixture of 2-methylthio-benzothiazole (18.4 g, 0.1 mol) and methyl-p-toluenesulfonate (76 mL, 0.5 mol) was heated to a temperature between 120° C. to 145° C. for 1 hour. After cooling to room temperature diethyl ether (200 mL) was added. The resulting solid was triturated with diethyl ether and isolated by filtration to give the crude product (42.7 g, quantitative). 1H-NMR (300 MHz, CDCl3): δ 8.12 (d, 1H), 7.92 (d, 1H), 7.62 (d, 3H), 7.3 (t, 1H), 7.02 (d, 2H), 4.05 (s, 3H); 3.0 (s, 3H), 2.23 (3, 3H).

Provenance & Evidence