Synthesis benzimidazole derivatives

Phan Tuyet Nu * , Bui Thi Buu Hue and Mai Van Hieu

* Corresponding author (ptnu91@gmail.com)

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Received: 20 Apr 2021
Accepted: 22 Dec 2016
Published: 23 Dec 2016
Title: Synthesis benzimidazole derivatives
DOI: 10.22144/ctu.jvn.2016.607
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How to Cite
Nữ, P. T., Huê, B. T. B., & Hiếu, M. V. (2016). Synthesis benzimidazole derivatives. CTU Journal of Science, (47), 107-113. https://doi.org/10.22144/ctu.jvn.2016.607
Issue
No. 47 (2016)
Section
Natural Sciences

Abstract

Ten benzimidazole derivatives with various substituents (aza, H, Cl, NO2, CH3) at the C4 and C5 positions on the benzimidazole heterocycles have been successfully synthesized from moderate to excellent yield (41% - 90%). The synthesis made use of a condensation between substituted o-phenylenediamines and benzylamines in the presence of Na2S2O5 as the oxidant. Dimethylsulfoxide (DMSO) proved to be the better solvent than ethanol for this transformation. Reaction time was shortened from 24 hours to 18 hours. 2‑(2‑Chlorophenyl)‑5‑nitro‑1H‑benzimidazole had the best synthetic performance (90%). The structures of these new compounds were confirmed by MS, 1H-NMR and 13C-NMR spectra.
Keywords: Benzimidazole, sodium metabisulfite, o-phenylenediamine và benzylamine, benzylamine

Tóm tắt

Mười dẫn xuất benzimidazole mang các nhóm thế khác nhau ở các vị trí số 4 và số 5 trên nhân benzimidazole (aza, -H, -Cl, -NO2, -CH3) đã được tổng hợp thành công với hiệu suất 41% - 90% từ sự ngưng tụ giữa các dẫn xuất o-phenylenediamine và benzylamine, sử dụng sodium metabisulfite (Na2S2O5)là tác nhân oxi hóa. Việc sử dụng dung môi dimethylsulfoxide (DMSO) thay cho ethanol giúp tăng hiệu suất tổng hợp cũng như rút ngắn thời gian phản ứng từ 24 giờ xuống còn 18 giờ cho mỗi phản ứng tổng hợp. Hợp chất 2-(2-chlorophenyl)-5-nitro-1H-benzimidazole cho hiệu suất tổng hợp cao nhất (90%). Cấu trúc của các chất tổng hợp được xác định bằng các phương pháp phổ nghiệm MS,1H‑NMR và 13C‑NMR.
Từ khóa: benzimidazole, sodium metabisulfite, o-phenylenediamine, benzylamine

Article Details

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