2-amino-n-(4-bromophenyl)benzamide → 3-(4-bromophenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

Participants

Reaction Steps

To a solution of 2-amino-N-(4-bromo-phenyl)-benzamide (3.75 g, 12.9 mmol) and 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (D) (2.50 g, 12.9 mmol) in anhydrous ethanol (75 mL) was added anhydrous copper (II) chloride (5.19 g, 38.6 mmol). The reaction mixture was stirred under reflux for 16 hours under nitrogen, then cooled to room temperature. The ethanol was evaporated under reduced pressure. The residue was taken in dichloromethane (300 mL) and the organic phase was washed with water (200 mL). The aqueous phase was then extracted with CH2Cl2 (2×200 mL). The combined organic phase was washed with brine (200 mL) and dried over anhydrous Na2SO4. The solvent was evaporated. The crude compound was purified by column chromatography (silica gel 230-400 mesh; 30-50% ethyl acetate in hexanes as eluent) to give the title compound (K) as white solid. Yield: 3.84 g (64%). MP 164-165° C. 1H-NMR (400 MHz, DMSO-d6): δ 8.33 (d, J=7.80 Hz, 1H), 7.82-7.80 (m, 2H), 7.55-7.45 (m, 3H), 7.04 (d, J=8.58 Hz, 2H), 6.98 (s, 2H), 3.94-3.90 (m, 2H), 3.82 (t, J=4.68 Hz, 2H), 2.17 (s, 6H), 2.13 (t, J=3.51 Hz, 1H). MS (ES+) m/z: 465.42 (97%) (M+1), 467.43 (100%) (M+3).

Provenance & Evidence