Aniline → HCID 18963769, compound

Participants

Reaction Steps

To 3-(1-methylethoxy)-2-benzofurancarboxylic acid (200 mg, 0.91 mmol) in 7 mL of dry tetrahydrofuran is added oxalyl chloride (0.095 mL, 1.09 mmol) followed by dimethylformamide (0.02 mL). The solution is stirred at room temperature for 1.75 hours, then aniline (0.50 mL, 5.46 mmol) is added. The solution is stirred at room temperature overnight then partitioned between ethyl acetate and 1N HCl . The organic layer is washed with saturated aqueous NaHCO3 and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography eluting with 4:1 hexane:ethyl acetate to provide 5-chloro-3-(1-methylethoxy)-N-phenyl-2-benzofurancarboxamide in 84% yield; mp=82°-83° C.

Provenance & Evidence