Azobisisobutyronitrile → 4'-bromomethyl-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-biphenylsulphonamide

Participants

Reaction Steps

Azobis(isobutyronitrile) (150 mg) and N-bromosuccinimide (1.68 g) were added to a solution of N-(isobutoxycarbonyl)- N-(3-methoxy-5-methylpyrazin-2-yl)-4'-methyl-2-biphenylsulphonamide (4.44 g) in carbon tetrachloride (150 ml). The mixture was heated under reflux for 4 hours and then allowed to cool and filtered. The filtrate was concentrated by evaporation and the residue was purified by flash chromatography on silica (150 g), eluting with 20% ethyl acetate in isohexane. Fractions containing the product were combined and evaporated to give 4'-bromomethyl- N-(isobutoxycarbonyl)- N-(3-methoxy-5-methylpyrazin-2-yl)-2-biphenylsulphonamide (3.67 g); 1H NMR (d6 -DMSO): 0.6 (s, 6H), 1.6-1.7 (m, 1H), 3.8 (d, 2H), 3.95 (s, 3H), 4.8 (s, 2H), 7.3-7.5 (m, 5H), 7.7-7.8 (m, 2H), 8.15 (s, 1H), 8.45-8.55 (m, 1H); mass spectrum (+ve FAB, methanolBA): 548 (M+H)+.

Provenance & Evidence