Interaction of dithiocarbamates based on nitrophenyl-containing 1,2-amino alcohols with various organyl halides

Abstract

This article studied the interaction of nitrophenyl-containing 1,2-amino alcohols (1-[(p-nitrophenyl)-2-amino]-1,3-propanediol and 2-(2-nitrobenzyl)-1-phenyl-2-aminoethanol) with carbon disulfide in the presence of potassium hydroxide or triethylamine to form salts of dithiocarbamic acids, which were further alkylated with various alkyl halides and acylated with benzoic acid chlorides.
In the course of the reaction, it was found that nitrophenyl-containing 1,2-amino alcohols showed different reactivity in acylation reactions. This was established in the reaction of the dithiocarbamic salt of 1-[(p-nitrophenyl)-2-amino]-1,3-propanediol with a benzoic acid chloride. As a result of the synthesis, it was not possible to obtain the expected main product. As a result, the structure of the resulting side compound was proved using the quantum chemical method and X-ray diffraction analysis. Quantum-chemical calculations and X-ray diffraction analysis are given in the work.