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The pathway in the formation of cyanogen chloride from the reaction of 1-naphthol (1) and 4-phenylimidazole with chloramine was investigated. The intermediates isolated in the reaction of 1-naphthol (1) with chloramine were N-chloro-1, 2-naphthoquinone 2-imine (2) and o-carboxycinnamonitrile (6), the latter of which, liberating cyanogen chloride, was finally converted tophthalide-3-carboxylic acid (8). The products obtained in the reaction of 4-phenylimidazole (10) with chloramine were benzonitrile (14), benzoylformic acid (22) and benzoic acid (23) besides cyanogen chloride. Cyanogen chloride formed by the reaction of 4-methylimidazole with [15N]- chloramine was C14NCl. From these results the pathway of cyanogen chloride formation was elucidated.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Formation of cyanide ion or cyanogen chloride through the cleavage of aromatic rings by nitrous acid or chlorine. X. Pathway of cyanogen chloride formation in the reactions of 1-naphthol and 4-phenylimidazole with chloramine.