SYNTHESIS OF ESTERS OF HALOGENOACETIC ACIDS

Amidoalkylating reagents containing a phthalimide group are used in the synthesis of hard-to-reach primary amines and complex heterocycliccompounds. These types of amidoalkylating compounds are suitable reagents for nucleophilic substituted reactions in acidic media due to their resistanceto acids. Result of reactions of amidoalkylating reagents-N-hydroxyethylphthalimide and N-hydroxymethylphthalimide with aliphatic carbonic acids canalso produce new bactericidal and fungicidal esters. In this study, halogen acids reacted with N-hydroxymethylphthalimide monochloric acetic acid, monobromicacetic acid, monoiodic acetic acid, trifluoric acetic acid and trichloroacetic acid, as well as, N-b-hydroxyethylphthaleidyl monohydric acid. As aresult of the reactions, new phthalimidomethyl and phthalimidoethyl esters of haloacetic acids were synthesized. The physical properties of crystallineesters have been determined. The structure of these compounds were confirmed by the analysis of their IR and PMR spectra. The esterification reactions ofhalogenated acetic acids were carried out in a benzene solvent and a sulfuric acid catalyst with primary alcohols, N-hydroxymethylphthalimide and N-β-beta hydroxyethylphthalimide,. It was found that in a benzene solvent, which increases the rate of bimolecular nucleophilic exchange in primary alcohols,phthalimidoethyl esters of halogen acid are formed in high yields, and phthalimidomethyl esters are formed in low yields. It was shown that the reaction ofesterification of halogen acids with N-hydroxymethylphthalimide proceeds with monomolecular nucleophilic exchange.