GB529055A - Manufacture of esters of oxyalkylamidines - Google Patents

Abstract

529,055. Amidine derivatives. SOC. OF CHEMICAL INDUSTRY IN BASLE. May 11, 1939, No. 14058. Convention date, May 11, 1938. Sample furnished. [Class 2 (iii)] Reactive esters of oxyalkylamidines, including cyclic amidines such as imidazolines and tetrahydropyrimidines, are made by reacting a reactive ester of a hydroxy carboxylic acid imido ether, imido halide or thioamide with ammonia or a primary or secondary amine in equimolecular proportions. The reactive esters are those derived from strong acids, e.g. hydrohalic and alkyl- or aryl-sulphonic acids ; the ester group takes no part in the reaction. In examples (1) 2-chloro- and 2-bromo-methylimidazoline hydrochlorides are made from chlor- (or brom-) acetimidoethyl ether hydrochloride and ethylenediamine, (2) 2-γ-chloropropyl-imidazoline hydrochloride is made from γ-chlorobutyroimidoethyl ether hydrochloride (made by the action of hydrochloric acid on a mixture of equivalent quantities of γ-chlorobutyronitrile and ethyl alcohol) and ethylenediamine, (3) chlor-acetpiperidine-amidine hydrochloride is made from chloroacetimidoethyl ether hydrochloride and piperidine ; the ptoluenesulphonic ester of hydroxy-acetpiperidine-amidine is similarly obtained, and (4) chloroacetamidine hydrochloride is obtained by reacting chloracetimidoethyl ether hydrochloride with ammonia in absolute alcohol. A sample has been furnished under Sect. 2 (5) of chloracet-#-phenylethylamidine hydrochloride, made from chloracetimidoether hydrochloride and #-phenylethylamine.