Synthesis of prodrugs and a mutual prodrug of chlorzoxazone and acetaminophen based on a masked benzoxazolone

A series of alkyl and aryl N-(5-chloro-2-hydroxyphenyl)carbamates, prodrugs of chlorzoxazone, have been synthesized. The synthesis in a five-step process of one of them, 4-acetamidophenyl ester, a mutual prodrug of chlorzoxazone and acetaminophen, is described.