GB497368A - New nitrogen-containing organic compounds - Google Patents

Abstract

Urea derivatives containing an amino or quaternary ammonium group are obtained by the action of an aliphatic, cycloaliphatic or araliphatic amine, or of a heterocyclic amine containing only one heterocyclic ring, on an ester derived from a hydroxyalkyl or hydroxyacyl urea and a hydrogen halide or aromatic sulphonic acid. Examples are given of the manufacture of products from (1) 2-chlorethylurea hydrochloride and pyridine; (2) chloracetylurea and piperidine; (3) iodoacetylurea and N-benzylpiperidine; (4) pyridine and the reaction product of b -hydroxyethylurea and p-toluenesulphochloride; the picrate derived from the product is identical with the picrate derived from the product of example 1; (5) chloracetylurea and pyridine; (6) chloracetylurea and diethylamine; (7) g -chloropropylurea and pyridine; (8) 2-chlorethylurea hydrochloride and triethylamine; and (9) chloracetylurea and piperidylacetylurea, made as described in example 2. An additional urea derivative which may be treated is a -chloropropionylurea, and additional amines which may be used are methylamine, ethylamine, dimethylamine, benzylamine, cyclohexylamine, N-methylpiperidine, a -picoline, quinoline and the tertiary amines obtainable by reaction of a halogenalkyl- or halogenacyl-urea with a secondary amine. 2-Chlorethylurea hydrochloride is obtained from 2-hydroxyethylurea and thionyl chloride. g -Chloropropylurea is obtained by warming g -aminopropanol with nitrourea, and treating the g -hydroxypropylurea so obtained with thionyl chloride.