Deprotection of acetyl group on amino group with thionyl chloride and pyridine
2012
Cao Yuqing, Hebei University, Baoding (China), College of Pharmacy | Du Dingxiang, Hebei University, Baoding (China), College of Pharmacy | Yang Xiaojun, Hebei University, Baoding (China), College of Pharmacy
[Objective] This study aimed to analyze the deprotection of acetyl group on amino group. [Method] A simple, convenient one-pot amino protection group of amide removed by thionyl chloride and pyridine via efficient chlorination and hydrolysis with 1, 2-dichloroethane as solvent at ambient temperature has been developed. [Result] Pyridine is crucial to the reaction; the best solvent is 1, 2-dichloroethane, and the most suitable reaction temperature is the ambient temperature; in addition, the yield is the highest as the molar ratio of pyridine to N-(4-bromophenyl) acetamide is 1:1. [Conclusion]The significant features of this protocol are short reaction times, cleaner reaction profiles, under mild reaction conditions and easy purification, and simple workup that precludes the use of toxic solvents.
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