Sulfuric Acid → HCID 22647966, compound

Participants

Reaction Steps

To a stirred suspension of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(1-hydroxy-1-methylethyl)-3,4-dihydroquinazolin-2(1H)-one (460 mg) in acetic acid (0.4 mL) was added bromoacetonitrile (0.1 mL). To this mixture was added concentrated sulfuric acid (0.2 mL) and the resulting solution was allowed to stir overnight. The reaction was quenched by dropwise addition of the mixture to a rapidly stirred mixture of 2N aqueous NaOH and CH2Cl2. Transferred to a separatory funnel, diluted with water and extracted 3× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone giving 2-bromo-N-{1-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methylethyl}acetamide.

Provenance & Evidence