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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
Author(s) -
Slomczyńska Urszula,
Barany George
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210147
Subject(s) - chemistry , sulfuryl chloride , thiocarbamates , chloride , organic chemistry , hydrolysis , aryl , benzoyl chloride , medicinal chemistry , alkyl
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 of equimolar 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.