4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde → 3-(4-sec-butylphenyl)-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-8-methoxyquinazolin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a 100-mL round bottom flask were added 2-amino-N-(4-sec-butyl-phenyl)-3-methoxy-benzamide (0.533 g, 1.79 mmol), 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde (0.382 g, 1.96 mmol), anhydrous copper (II) chloride (0.722 g, 5.37 mmol), and anhydrous ethanol (40 mL). The mixture was refluxed at 100° C. under N2 for 5 hours. The mixture was concentrated to dryness. Water (approximately 20 mL) was added and extracted with EtOAc (3×50 mL). The EtOAc solutions were combined and dried over Na2SO4. The crude product was purified by column chromatography on silica gel using hexane/EtOAc (1:1 to 1:2) as eluent. The product fractions were concentrated to dryness then re-crystallized in ether to afford the title compound as white solid. Yield: 0.460 g (54%). MP 158-159° C. 1H-NMR (400 MHz, CDCl3): δ 7.93 (d, 1H), 7.46 (t, 1H), 7.24 (d, 1H), 7.12 (d, 2H), 7.05 (d, 2H), 7.00 (s, 2H), 4.03 (s, 3H), 3.89 (m, 2H), 3.75 (m, 2H), 2.56 (m, 1H), 2.11 (s, 6H), 1.52 (m, 2H), 1.19 (d, 3H), 0.72 (t, 3H). MS (ES+) m/z: 473.27 (M+1).

Provenance & Evidence