Imidazole → HCID 136375566, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 2-(5-bromo-2-n-propoxy-phenyl)-8-methylquinazolin-4(3H)-one (Preparation 11; 0.6 g, 0.0016 mol), anhydrous potassium carbonate (0.22 g, 0.0016 mol), copper bronze (0.1 g, 0.0016 mol), iodine (0.051 g 0.004 mol), imidazole (0.55 g, 0.008 mol) and 1-methyl-2-pyrrolidinone (20 ml) was heated at 180° C. under a nitrogen atmosphere for 6 hours. The mixture was cooled and poured into water (150 ml), then the resulting mixture extracted with a dichloromethane-methanol mixture (9:1, 4×40 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum. The semi-solid residue was chromatographed on silica gel (10 g) using a methanol in dichloromethane elution gradient (0-4%). Evaporation of the appropriate fractions gave the title compound which crystallized from ethyl acetate as colorless needles (0.016 g, 3%); Rf 0.5 (silica; dichloromethane-methanol 95:5).

Provenance & Evidence