Benzoyl Peroxide → 2-Acetoxymethyl-6-bromomethyl-7-chloro-3,4-dihydroquinazolin-4-one

Participants

Reaction Steps

To a suspension of 2-acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one (2.00 g, 7.5 mmol) in anhydrous carbon tetrachloride (120 ml) was added N-bromosuccinimide (1.47 g, 8.3 mmol) followed by dibenzoyl peroxide (7.0 mg) under argon. The reaction mixture was placed in a preheated oil bath at 120° C. and stirred at this temperature for 3.5 hours while illuminating. The solvent was removed in vacuo and the residue was twice purified by column chromatography using 40% ethyl acetate in chloroform as eluant (1.02 g, 40%), mp 190-195° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 4.91, 4.97 (2×s, 4H, 2-CH2 and 6-CH2), 7.78 (s, 1H, 8-H), 8.36 (s, 1H, 5-H), 12.61 (s, 1H, N3—H). This product was used in the next experiment without any further purification.

Provenance & Evidence