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Abstract
AbstractCondensation of chlorocarbonylsulfenyl chloride 1 with 1‐(5‐(1,1‐dimethylethyl)‐1,2‐oxazol‐3‐yl)‐3‐methylurea 4a has been found to give isomeric 2,4‐disubstituted‐1,2,4‐thiazolidine‐3,5‐diones 5 and 6. Assignments are confirmed by the X‐ray structure data of 6. Sulfenylation with alkoxycarbonylsulfenyl chlorides 7 and trichloromethylsulfenyl chloride 10 of 4 occurs exclusively on N‐1 rather than N‐3 of the urea moiety. With the isomeric 1‐[3‐(1,1‐dimethylethyl)‐1,2‐oxazol‐5‐yl]‐3‐methylurea 14 and ethoxycarbonylsulfenyl chloride 7b, C‐sulfenylated derivatives 15 and 16 are formed in low yield.
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