The reaction of formaldehyde with mixtures of arylhydrazines and amines

Abstract

Phenylhydrazine, aniline and formaldehyde react under appropriate conditions to give a high yield of phenyl(phenylazoethyl)amine (1). Under analogous conditions N-methyl-N-phenylhydrazine, N-methylaniline and formaldehyde give 2-(N-methy1anilino)acetaldehyde methylphenylhydrazone (2). With morpholine and phenylhydrazine formaldehyde gives a product C₂₄H₃₄N₆O₂ considered from spectroscopic evidence to be 2,5-di(morpholinomethyl)-1,4-diphenylhexahydro-s-tetrazine (4) derived from an N-Mannich reaction between morpholine and 1,4-diphenylhexahydro-s-tetrazine.A change in the relative proportions of phenylhydrazine, aniline and formaldehyde results in the formation of a further compound C₄₄H₄₆N₁₀ considered from spectroscopic data to be 2,5-di[Nphenyl-N-(phenylazoethyl)aminomethyl]-l,4-diphenylhexahyo-s-tetrazine (7) derived from an N-Mannich reaction between phenyl(phenylazoethyl)amine (1) and 1,4-diphenylhexahydro-stetrazine.