Trifluoroacetic acid → HCID 57819988, compound

Participants

Reaction Steps

To a solution of 4-bromobenzaldehyde (3.09 g, 16.7 mmol) in anhydrous MeOH (10 mL) was added N-aminoethyl-morpholine (2.17 g, 16.7 mmol) followed by trifluoroacetic acid (1.90 g, 16.7 mmol) under N2 atmosphere. After stirring the reaction mixture for 5 minutes, 4-trifluoromethylphenylisocyanide (2.85 g, 16.7 mmol) was added and the reaction then heated to 80 degrees Celcius for 2 h. Anhydrous potassium carbonate (4.60 g, 33.3 mmol) was then added and the reaction stirred at 80 degrees Celcius for an additional 2 h. After solvent removal, the residue was diluted with dichloromethane (100 mL) and water (100 mL). The aqueous layer was extracted with dichloromethane (50 mL x2). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with ethyl acetate: petroleum ether gradient (10%-50%) to afford the product as a yellow solid (2.9 g, 35%).

Provenance & Evidence