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■ Synthesis of 5-Chloromethylene Hydantoins and Thiohydantoins

Timothy A. Cernak and James L. Gleason*

*Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A 2K6, Canada

Abstract

5-Chloromethylene hydantoins were prepared by condensation of ureas with chloropyruvic acid. 5-Chloromethylene thiohydantoins were prepared by chlorination of dehydroalanines followed by condensation with thiophosgene. Convenient methods for formation of aminomethylene hydantoins and thiohydantoins using N,N,N’,N’-tetramethylformamidinium chloride are also reported.