Benzoyl Peroxide → HCID 135838176, compound

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Reaction Steps

To a solution of N-(6-methyl-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (1.76 g, 5.7 mmoles) in dry benzene (150 ml) was added N-bromosuccinimide (1.01 g, 5.7 mmoles) and dibenzoyl peroxide (15 mg). The mixture was heated to reflux under a nitrogen atmosphere for 2.5 hours. After cooling, benzene was removed under reduced pressure, and the residue was purified on a silica gel column eluting with chloroform to give N-(6-(bromomethyl)-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide as an off-white solid. (1.4 g, 57%) 1H NMR (DMSO-d6, 200 MHz) δ: 1.27 (s, 9H, t-butyl); 5.26 (s, 2H, CH2Br); 7.63-7.81 (m, 3H, Ar); 8.26 (dd, J=7.6, 2.0 Hz, 1H, Ar); 9.81 (dd, J=7.8, 2.0 Hz, 1H, Ar); 11.27 (s, 1H, NH); 12.33 (s, 1H, NH). Anal. Calculated for C18H18BrN3O2: C, 55.68; H, 4.67; N, 10.82. Found C, 55.48; H, 4.84; N, 10.57.

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