Oxalyl chloride → HCID 44250625, compound

Participants

Reaction Steps

380 mg (2.2 mmol) of (2-[(4-chloro-2-(methoxycarbonyl)phenyl)amino]-2-oxoethoxy)acetic acid was dissolved in 7 mL of THF. 361 mg (2.9 mmol) of oxalyl chloride and a catalytic quantity of DMF were added thereto under ice-cooling, and stirred at room temperature for 2 hours. Thereafter, the solvent was distilled off under reduced pressure. The DMA solution of 380 mg (2.2 mmol) of 3-(5-methylfuran-3-yl)aniline was added to the resulting residue, and stirred for 1 hour. After completion of the reaction, an aqueous sodium bicarbonate solution (was added dropwise, and extraction was carried out using ethyl acetate. The organic layer was washed with an aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give 5-chloro-2-([(2-([3-(5-methylfuran-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 32%).

Provenance & Evidence