A New Industrial Process for 10-Methoxyiminostilbene: Key Intermediate for the Synthesis of Oxcarbazepine

Abstract

A new industrial process, involving only two isolation and drying steps, for 10-methoxyiminostilbene (MISB), an advance intermediate of widely prescribed antiepileptic drug, oxcarbazepine, has been developed. A salient feature of this process is the novel use of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) to afford bromohydrin methyl ether from N-acetyliminostilbene. The byproducts of this process namely acetic acid, 5,5-dimethylhydantoin and Et3N·HBr are recyclable as well as nontoxic. This process is amenable for the large-scale production of MISB.