Dehydration Reactions of Benzaldoxime by Means of Compounds Having a Nitrogen-Carbon Double Bond

The dehydration reactions of benzaldoxime with such nitrogen-carbon double bond compounds having halogen and alkoxyl groups as phenylimidophosgen, ethyl N-phenyliminochlo-roformate and ethyl N-phenylformidate were studied. One mole of phenyl imidophosgene, when reacted with 1 mol. of benzaldoxime, gave phenyl isocyanate and benzonitrile as main products. On the other hand, with 2 mol. of the aldoxime, aniline hydrochloride and benzonitrile were obtained in good yields. The aldoxime was also dehydrated effectively by ethyl N-phenyliminochloroformate to give, among other byproducts, the nitrile and ethyl N-phenylcarbamate. The nitrile and formanilide were obtained by the reaction of the aldoxime with ethyl N-phenylformidate.