N-Aroylbenzimidazoles as efficient new reagents for a greener esterification reaction under solvent-free conditions

Baramee  Phungpis; Kanokkan  Worawut

Authors

Baramee Phungpis Faculty of Natural Resources, Rajamangala University of Technology Isan Sakonnakhon Campus, Sakonnakhon 47160, Thailand
Kanokkan Worawut Faculty of Natural Resources, Rajamangala University of Technology Isan Sakonnakhon Campus, Sakonnakhon 47160, Thailand

Keywords:

N-aroylbenzimidazoles, aroylation reagent, esterification, grinding.

Abstract

Due to the increasing demand for green technology and its numerous advantages over conventional methodologies, this work has received interest for the development of a facile and efficient method for the synthesis of esters using benzimidazole chemistry. N-aroylbenzimidazole derivatives 2a-d synthesized herein were found to be highly active acylation reagents, readily leading to high-yielding syntheses of ester products under solvent-free conditions without the need for a catalyst. A wide variety of esterification reactions between alcohols 1a-e and N-aroylbenzimidazoles 2a-d were carried out by grinding the mixtures, which were converted to their ester products 3a-t in a simple synthetic procedure with yields in the range of 84% to 96% and recovery of the by-product benzimidazole (4) (80-93%). Compound 4 can be reused for the preparation of N-aroylbenzimidazoles 2a-d without significant loss of efficiency. The advantages of this current methodology are the simple procedure; the absence of hazardous organic solvents; catalyst- and solvent-free conditions with high yields, low reaction temperatures, and short reaction times; and eco-friendly reactions generating no waste and allowing reagents to be recovered and reused.

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