Hydrochloric Acid → HCID 13723405, compound

Participants

Reaction Steps

Under nitrogen atmosphere, BOP-Cl (5.09 grams, 0.02 mol) was added in one portion to a well-stirred solution of 2-anilino-4-oxo-3-furoic acid (4.38 grams, 0.02 mol) and triethylamine (2.8 ml, 20 mmol) in 34 ml methylene chloride, at 0° C. The reaction mixture was stirred at 0° C. for 45 min after which time 2.35 grams (0.022 mol) of p-toluidine in 17 ml methylene chloride were added over a period of 15 min. followed by the dropwise addition of triethylamine (2.8 ml, 20 mmol). The reaction mixture was stirred at 5°-10° C. for 30 min and at room temperature for 2 hours, poured into ice-water, acidified with 2N hydrochloric acid (pH 1), and then extracted with methylene chloride. The organic extract was washed with 5% aqueous sodium bicarbonate solution, dried over sodium sulfate, and the solvent evaporated under reduced pressure leaving the crude product which was recrystallized from ethanol. Yield: 3.37 grams, mp 181°-183° C. (R=C6H4CH3 --p).

Provenance & Evidence