Chloroacetonitrile → Methyl 2-[(Cyanomethyl)thio]benzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl thiosalicylate (164 g, 0.975 mol) in methanol (1.1 L) was added in one portion to a cold solution of freshly prepared sodium methoxide (from 25.5 g, 1.1 mol Na-metal in methanol, 1.1 L). The salt solution was cooled to 0° C. and a cold (0° C.) solution of chloroacetonitrile (83.7 g, 1.1 mol) in methanol (0.5 L) was added in one portion with stirring. After several minutes a strong precipitate appeared. After standing for several days at room temperature, the precipitate was collected, washed with ice-cold methanol, then washed well with water and dried to give 141.0 g of 2-(2-carbomethoxyphenylthio)acetonitrile, mp 120°-122° C. [described by K. Gorlitzer, Arch. Pharmaz., 308, 700 (1975)].

Provenance & Evidence