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Chemistry of sulfonyl isocyanates and sulfonyl isothiocyanates. IX . Routes to substituted oxazolidin‐2‐ones and oxazolidine‐2‐thiones
Author(s) -
Mcfarland J. W.,
Hayes C. E.,
Blair E. B.,
Stuhlmacher K. R.
Publication year - 1980
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.5570170213
Subject(s) - chemistry , sulfonyl , isocyanate , pyridine , oxazolidine , thiocarbamate , carbamate , isothiocyanate , medicinal chemistry , organic chemistry , chlorobenzene , hydrolysis , sulfonamide , sodium hydroxide , alkyl , polyurethane , catalysis
4‐Chlorobenzenesulfonyl isocyanate (I) reacted with 2‐chloroethanol and 1‐chloro‐2‐propanol to give, respectively, 2‐chloroethyl 4‐chlorobenzenesulfonyl carbamate (III) and 1‐chloro‐2‐propyl 4‐chlorobenzenesulfonyl carbamate (VI). The carbamates III and VI cyclized under the influence of pyridine to afford, respectively, 3‐(4‐chlorobenzenesulfonyl)oxazolidin‐2‐one (IV) and 3‐(4‐chlorobenzenesulfonyl)‐5‐methyloxazolidin‐2‐one (VII). The oxazolidin‐2‐ones were stable toward hydrochloric acid but hydrolyzed in 2 M sodium hydroxide solution to N ‐(2‐hydroxyethyl)‐4‐chlorobenzenesulfonamide (V) and N ‐(2‐hydroxy‐1‐propyl)‐4‐chlorobenzene‐sulfonamide (VIII), respectively. 4‐Toluenesulfonyl isothiocyanate (II) reacted with 2‐chloroethanol to give 2‐chloroethyl 4‐chlorobenzenesulfonyl thiocarbamate (IX), which was converted by pyridine to 3‐(4‐toluenesulfonyl)oxazolidine‐2‐thione (X).