The decomposition of thionyl chloride in the presence of ammonia was found to give sulphur, ammonium sulphate, and ammonium sulphamate besides ammonium chloride. Heating urea and the reaction products of thionyl chloride and ammonia under pressure yielded guanidine hydrochloride and melamine, under different conditions of temperature, time, and pressure. Under similar conditions, benzamide was transformed into benzonitrile, and phenylurea into aniline or aniline black and diphenylurea, guanidine being absent.
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Gagnon et al. (1959) studied this question.