Dichloromethane → methyl N-(4-bromophenyl)-N-(3,5-dimethylbenzyl)oxamate

Participants

Reaction Steps

Methyl chloroglyoxylate (0.566 ml, 6.16 mmol) was added dropwise to a mixture of 4-bromo-N-(3,5-dimethylbenzyl)aniline (1.49 g, 5.13 mmol), triethylamine (1.08 ml, 7.70 mmol) and dichloromethane (20 ml) at 0°, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (1.66 g, 86%) as a pale yellow oil.

Provenance & Evidence