Chloroacetonitrile → p-Cyanothiobenzoic Acid S-Cyanomethyl Ester

Participants

Reaction Conditions

Reaction Steps

Chloroacetonitrile (13.1 ml; 0.203 mol) is added over 15 minutes to a cold (15° C.) 2 N solution of sodium trithiocarbonate (92.5 ml; 0.185 mol). The reaction mixture is stirred one hour at 5° C., extracted with ether, and the aqueous layer added dropwise to a solution of p-cyanobenzoyl chloride (20.9 g; 0.124 mol) in dichloromethane (40 ml). During addition, the temperature of the reaction mixture is held below 12° C. The reaction mixture is then held at 0°-5° C. for 2 hours, diluted with hexane (50 ml) and filtered to yield 26 g of a yellow solid. This solid is recrystallized from a mixture of acetone-methanol-water to afford 19.7 g of title product, a yellowish solid, melting point 129°-131° C.

Provenance & Evidence