Formation of N‐Sulfonylcarbamates from Epichlorohydrin: Synthesis of Polyfunctional Oxazolidin‐2‐ones

Abstract

The addition of 3‐methylbut‐2‐enoic acid‐3‐bromo‐2‐hydroxypropyl ester 2 and 1‐bromo‐3‐phenylsulfanyl propan‐2‐ol 3, obtained from epichlorohydrin, to aroxy and alkoxysulfonyl isocyanates 1 in anhydrous ether at ambient temperature affords the corresponding N‐sulfonyl bromocarbamates 4. These are treated with triethylamine in refluxing acetone to give exclusively the corresponding polyfunctional oxazolidin‐2‐ones 5 with good yields.

Keywords:

• aroxy and alkoxysulfonyl isocyanates
• N‐sulfonyl bromocarbamates
• oxazolidin‐2‐one