Azobisisobutyronitrile → N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(3-chlorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.0 g), N-bromosuccinimide (0.45 g), azobis-isobutyronitrile (10 mg) in carbon tetrachloride was heated at 65° C. for 2 hours. A second addition of N-bromosuccinimide (0.1 g) was made and the solution heated at 65° C. for a further 2 hours. The solution was then allowed to cool and the solvent removed under reduced pressure to give a brown residue, which was purified by dry column chromatography on silica, eluting with ethyl acetate/dichloromethane to give N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 8, 0.1 g) as a white solid, m.p. 89.8-90.8° C.

Provenance & Evidence