GB792791A - A process of preparing substituted amides and intermediates therefor - Google Patents

Abstract

Compounds of the formula <FORM:0792791/IV (b)/1> (wherein the benzene nucleus may be substituted by alkyl groups, X is a bivalent aliphatic hydrocarbon radical and Hlg is a halogen atom) are prepared by heating a monohalogenated fatty acid Hlg.X.COOH with an anilide of the formula <FORM:0792791/IV (b)/2> where Z is a monovalent hydrocarbon radical. This process may be combined with the further step of replacing the halogen atom in the product by a mono- or di-substituted amino group, by reaction with a primary or secondary amine. The first process is advantageously conducted at 150 DEG to 200 DEG C., preferably while passing a stream of dry hydrogen chloride gas through the reaction mixture. In examples: (1) acetyl-xylidine-2:6 and monochloroacetic acid are heated together and the reaction product is taken up in benzene and heated with diethylamine to give diethylaminoacetyl-xylidine-2:6, identified as the bioxalate and the picrate; (2) butyryl-xylidine-2:6 replaces the acetylxylidine of (1), the final product being identical with the bioxalate of (1); (3) aceto-o-toluidide replaces the acetyl-xylidine of (1), the final product being diethylaminoaceto-o-toluidide bioxalate; (4) the process of (1) is repeated except that dry HCl is passed through the reaction mixture, the yield thereby being increased. Reference is also made to the reaction of N-butyryl-xylidine-2:6 with alpha-chloro-iso-butyric acid to give N-(chloro-iso-butyryl)-xylidine - 2:6. Specifications 634,072 and 634,073 are referred to.