1,1'-Carbonyldiimidazole → HCID 67189327, compound

Participants

Reaction Steps

To a stirred solution of 5-bromo-2-(2-chlorophenylamino)benzonitrile (0.8201 g, 2.67 mmol) in THF (10.00 ml, 2.67 mmol) was slowly added borane-THF (10.7 ml, 10.7 mmol) at RT for 10 min and the resulting mixture was stirred continuously over night. The mixture was quenched with slow addition of MeOH until all bubbling subsided. The mixture was concentrated in vacco. The residue was diluted with NaHCO3(aq) and water (5 mL each) and the separated aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to give the crude residue, which was taken up in THF (8.00 ml) and treated with di(1H-imidazol-1-yl)methanone (0.519 g, 3.20 mmol) at RT. After stirring for 30 min, to the mixture was added potassium 2-methylpropan-2-olate (0.748 g, 6.67 mmol). The suspension was stirred at RT for 1 h and washed with EtOAc-ether to give 6-bromo-1-(2-chlorophenyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. MS m/e 336 (M+H)+.

Provenance & Evidence