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Efficient Synthesis of 1,2,4-Dithiazolidine-3,5-diones (Dithiasuccinoyl-amines) and Observations on Formation of 1,2,4-Thiadiazolidine-3,5-diones by Related Chemistry
Slomczynska, Urszula,Barany, George
, p. 241 - 246 (2007/10/02)
An efficient synthesis of 1,2,4-dithiazolidine-3,5-diones (1) from chlorocarbonylsulfenyl chloride (3) plus O-dimethylaminoethyl-N-alkyl or aryl thiocarbamates (4) has been worked out.In this synthesis, 1,2,4-thiadiazolidine-3,5-diones (5) have been shown to arise as low-level-by-products, and experiments were conducted to elucidate the mechanism of the side reaction.N,N'-Dimethyl-1,2,4-thiadiazolidine-3,5-dione (5a) was prepared in one step from N,N'-dimethylurea plus 3, or from 4a plus one equivalent of sulfuryl chloride.A general route to 5 involved reaction ofequimolar amounts of isocyanates (6), isothiocyanates (7) and sulfuryl chloride followed by hydrolysis of intermediate 9.Heterocycles reported have been characterized by nmr, ir, uv, ms, and hplc.
