Dicyclohexylcarbodiimide → Ethyl 3-[(3,5-dichlorophenyl)amino]-3-oxopropanoate

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Reaction Steps

In 200 ml of methylene chloride were dissolved 5.0 g of monoethylmalonate and 6.12 g of 3,5-dichloroaniline. Under cooling with ice, to the mixture was added 8.57 of N,N'-dicyclohexylcarbodiimide, followed by stirring at room temperature for 5 hours. Insoluble materials were removed by filtration. The filtrate was diluted with ethyl acetate, washed with 1N hydrochloric acid and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (silica gel:250 g) using a mixed solvent of chloroform and acetone (20:1 by volume) to obtain 6.57 g of the oily titled comouond.

Provenance & Evidence