1-Hydroxyethyl-2-substituted phenoxymethyl benzimidazoles: synthesis and crystal structures. | [Journal of Chemical Society of Pakistan • 2016]

Author(s):

1. Jiacheng Wu: Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu, China; National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu, China

2. Li Zhao: Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu, China;National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu, China

3. Changqing Zhao: College of Bioengineering, Sichuan University of Science and Engineering, Zigong, China

4. Zhiyuan Wang: Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu, China;National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu, China

5. Haibin Gu: Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu, China; National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu, China

6. Wuyong Chen: Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu, China; National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu, China

Abstract:

Five novel 1-hydroxyethyl-2-substituted phenoxymethyl benzimidazoles c1-c5 were successfully synthesized by a three-step route. Firstly, five substituted phenoxymethyl acids a1-a5 were prepared by the O-carboxymethylation reaction of the starting substituted phenols under microwave irradiation. Then, these compounds reacted with o-phenylendiamine to get the key intermediates 2-substituted phenoxymethyl benzimidazoles b1-b5. At last, the target compounds were synthesized by the N-hydroxyethylation reaction of b1-b5 with 2-chloroethyl alcohol through the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst. The structures of the target compounds were well characterized and verified by elemental analysis, MS, IR, 1H NMR, 13C NMR and single crystal X-ray diffraction analysis.

Page(s): 307-312

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 38, Issue: 2, Year: 2016

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