GB698543A - Imino-ethers and their acid addition salts - Google Patents

Abstract

The invention relates to imino ethers having the general formula <FORM:0698543/IV (b)/1> wherein X represents an oxygen or sulphur atom and R represents the residue of an alcohol or mercaptan RXH and is preferably an alkyl group having up to 4 carbon atoms, and the corresponding acid addition salts. The compounds may be prepared by treating an anhydrous solution or suspension in a liquid diluent of dichloracetonitrile and an alcohol or mercaptan R.XH with dry hydrogen chloride or bromide, the reaction mixture being cooled, and if the free ether is desired, basifying the resulting acid addition salt of the ether thus obtained by treatment with an organic base in the absence of water. The compounds may be used as intermediates in the production of oxazolines as described in Specification 698,542. In examples, (1) dichloroacetonitrile is dissolved in a dry mixture of ether and ethyl alcohol, the solution is cooled in a freezing mixture and saturated with dry hydrogen chloride and crystalline dichloro acetamino ethyl ether hydrochloride separates; it is identified by conversion into dichloracetamidine picrate by reaction with saturated alcoholic ammonia and then with saturated alcoholic picric acid; the free imino ether is obtained from the hydrochloride by treatment with dry pyridine in ether; (2) a solution of dichloroacetonitrile and ethyl mercaptan in anhydrous chloroform is saturated with dry hydrogen chloride and dichloro acetamino ethyl thioether hydrochloride is recovered and converted into the base by the method of (1). Other starting materials mentioned are cyclohexanol, phenyl ethyl alcohol and tetrahydrofurfuryl alcohol and the corresponding mercaptans; in general aliphatic, cycloaliphatic, aralkyl or heterocyclic compounds containing alcoholic hydroxyl or mercapto groups may be used.