63924-75-4Relevant articles and documents
Chemistry of Sulfonyl Isocyanates and Sulfonyl Isothiocyanates. IX. Routes to Substituted Oxazolidin-2-ones and Oxazolidine-2-thiones
McFarland, J. W.,Hayes, C. E.,Blair, E. B.,Stuhlmacher, K. R.
, p. 271 - 272 (2007/10/02)
4-Chlorobenzenesulfonyl isocyanate (I) reacted with 2-chloroethanol and 1-chloro-2-propanol to give, respectively, 2-choroethyl-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 2M sodium hydroxide solution to N-(2-hydroxyethyl)-4-chlorobenzenesulfonamide (V) and N-(2-hydroxy-1-propyl)-4-chlorobenzenesulfonamide (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).