Ethyl 4-cyanobenzoate → Ethyl 5-(4-ethoxycarbonylphenyl)-1,2,4-thiadiazole-3-carboxylate

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Reaction Steps

A solution of 1.75 g (0.010 mol) of ethyl 2-oxo-1,3,4-oxathiazole-5-carboxylate and 17.5 g (0.10 mol) of ethyl p-cyanobenzoate was stirred at 190° C for 72 hours, cooled, and dissolved in acetone. Gc analysis of the solution revealed that the product had formed in 53% yield. Concentration of the solution to 90° C (0.1 torr) and two crystallizations of the residue from ethanol (charcoal) at -20° C gave 0.72 g (23.5%) of beige solid, mp 66°-67.5° C.

Provenance & Evidence