THE PREPARATION OF β-ARYLOXYETHYLTRIA. LKYLAMMONIUM SALTS

A series of β-aryloxyethyltrialkylammonium salts was prepared for anthelmintic tests. Phenols carrying various substituents on the benzene ring (o-CH₃,p-CH₃, p-C₆H₅, o-NO₂, p-NO₂, 2-CH₃-5-CH(CH₃)₂), on being refluxed with dimethylamino- or diethylaminoethyl chloride in acetone solutions in the presence of anhydrous potassium carbonate, formed the corresponding β-aryloxyethyldimethylamines or β-aryloxyethyldiethylamines. An alternative route for the synthesis of such compounds was the formation of β-aryloxyethyl bromide by the action of excess of ethylene bromide on the corresponding phenols, followed by the condensation of the bromides with dimethylamine or diethylaminc. The tertiary amines so prepared readily reacted with methyl iodide, benzyl bromide or p-nitrobenzyl bromide, forming the expected quaternary ammonium salts. β-(p-Nitrophenylmercapto)-ethyltrimethylammonium bromide was prepared by the reaction of β-(p-nitrophenylmercapto)-ethyl bromide with trimethylamine.