Methyl 2-([3-(chloromethyl)benzoyl]amino)thiophene-3-carboxylate synthesis

Yield:648859-85-2 100%

Reaction Conditions:

with pyridine in dichloromethane at 0; for 1 h;

Steps:

H

2-Amino-thiophene-3-carboxylic acid methyl ester (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (100 ml). Subsequently, pyridine (2.4 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.8 ml) were added to the solution at 0°C, and the mixture was stirred at 0°C for one hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate and was then concentrated. The residue was purified by column chromatography using a hexane-acetone system to give 2-(3-chloromethyl-benzoylamino)-thiophene-3-carboxylic acid methyl ester as a useful intermediate (4.7 g, yield 100%).

References:

EP1614676,2006,A1 Location in patent:Page/Page column 175