p-Tolunitrile → Ethyl 5p-Tolyl-1,2,4-Thiadiazole-3-Carboxylate

Participants

Reaction Steps

A solution of 7.48 g (0.0427 mol) of ethyl 2-oxo-1,3,4-oxathiazole-5-carboxylate and 50.0 g (0.427 mol) of p-tolunitrile (redistilled) was held at 190° C for 72 hours. The reaction mixture, which contained the product in 16% yield, was concentrated under vacuum to 90° C (0.5 torr) to give 4.4 g of black residue. Elution chromatography of this material on 200 g of silica gel (Woelm, for dry column chromatography) with benzene gave 1.7 g of product. Crystallization of this material from hexane (charcoal) gave 0.72 g (7%) of solid, mp 65°-66.5° C.

Provenance & Evidence