ISSN 0005-2531 (Print) ISSN 2522-1841 (Online)
ACYLATION OF BENZIMIDAZOLINE-2-ONES WITH AROMATIC ACIDS CHLORIDES IN THE PRESENCE OF SMALL AMOUNTS OF FERRIC CHLORIDE HEXAHYDRATE
Y.R.Takhirov, A.R.Shonazarov, R.Sh.Kuryazov, D.A.Dushamov, S.B.Sadikova, N.Kh.Musulmonov

 

Among benzazoles, biologically active substances with a variety of important properties have been discovered, which are used in agriculture, medicine and other fields. To synthesize new organic compounds based on benzimidazolin-2-ones, determine the relative activity series of the aromatic acid chlorides involved in the reaction, determine the reaction duration, and determine the amount of catalyst used, the reactions of benzimidazolin-2-ones (Ia, b) with aromatic acid chlorides (IIa–h) in the presence of FeCl3∙6H2O. Based on the yield of 5(6)-aroylbenzimidazolin-2-ones formed in the acylation reactions, optimal conditions for the acylation reaction were found, according to which the ratio of reagents Ia,b:IIa-h:FeCl3∙6H2O = 1:1.2:1∙10-2, the reaction temperature was 200-205°C, the reaction duration was 3 hours. Under these conditions, the yield of 5(6)-aroylbenzimidazolin-2-ones (IIIa-p) was 40-79%. It was shown that the yield of the products depends on the degree of nucleophilicity of the benzimidazolin-2-ones and the degree of electrophilicity of the acylating agent. A number of relative activities of various substituted benzoyl chlorides were also found. The structure of the synthesized compounds was confirmed by IR, 1H NMR spectroscopy, mass spectrometry and elemental analysis.

doi.org/10.32737/0005-2531-2026-1-64-73

Keywords : benzimidazolin-2-ones, aromatic acid chlorides, acylation, alkylation, catalyst, 5-aroylbenzimidazolin-2-ones
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