Abstract
This work is aimed at studying the reaction of nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with amines and a rhodanide ion and developing methods of synthesizing a 2-(2'-acyloxy-ethoxy) ethylchlorides, rhodanides, and their derivatives previously unknown in specialized literature. In the chlorohydrin molecule of diethylene glycol, there are two reaction centers that allow carrying out nucleophilic substitution reactions, as well as reactions that promote them with electrophilic reagents. The authors carried out several experiments for acylating diethylene glycol chlorohydrine with carbonic acids, reactions of nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with various amines as well as synthesized the chloracetoxyethyl ether of rhodane acetic acid. While studying the nucleophilic substitution of 2-(2'-acyloxy-ethoxy) ethylchlorides with the rhodanide ion, it was discovered that only the chlorine atom was replaced. The possibility of the nucleophilic substitution of the ethylene chlorohydrine was shown by the example of N-methyl and N-ethylanilines. It was discovered that the hydroxyl group of diethylene glycol could react with carbonic acids in the presences of catalysts and, therefore, encourage esterification. It has been found out that the nucleophilic substitution of the chlorine atom in 2-(2'-acyloxy-ethoxy) ethylchlorides with the rhodanide ion goes smoothly in the presence of potassium iodide acting as an activator and that the acyloxy group is unaffected. It has been discovered that the primary role in the nucleophilic substitution of alcoxyalkylhalides is played by the basicity of amines and the essence and position of substituents relative to the alcoxyl group of the haloid atom.