Diethyl Ether → HCID 18928139, compound

Participants

Reaction Steps

To a solution of 2-(1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (17.00 g; 74.8 mmol; 1 eq) in anhydrous 1,2-dichlorobenzene (375 mL), commercially available carbonyldiimidazole (24.72 g; 149.7 mmol; 2 eq) is added under an argon atmosphere. This reaction mixture is allowed to stir under reflux for 2 hours. The expected quinoxalinone precipitates as a grey powder during the reflux. The initial crystal clear solution quickly turns black after heating and becomes non homogeneous. This crude reaction mixture is allowed to precipitate at 4° C. during 48 hours. The grey powder formed is then filtered off on a fritted glass. This solid is transferred in a 1 L flask, diluted in fresh ethyl acetate (500 mL) and heated to gentle reflux for two hours. Hot filtration and then several washings of the solid with diethyl ether afforded the title compound (14.28 g; 56.4 mmol; 75%) as a grey powder.

Provenance & Evidence