Liu Dong-zhi
2005
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Journal
Fine chemicals
Abstract
Synthesis of N-(6-chloro-4-methylthio-1-oxo-isochroman-5-yl)-trifluoroacetamide,the key intermediate for an indole,was studied.Started from 2-chloroethanol,2-(methylthio)ethyl pivalate was obtained via neucleophilic substitution with sodium methanethiolate and esterification with pivaloyl chloride in overall yield of 92.2%.Treatment of 3-amino-4-chlorobenzoic acid with trimethoxymethane generated methyl 3-amino-4-chlorobenzoate in 80.0% yield.2-(Methylthio)ethyl pivalate was oxidized by sulfuryl chloride,and then reacted with methyl 3-amino-4-chlorobenzoate followed by rearrangement,hydrolysis and acylation to give the title compound in overall yield of 25.8%.