Sodium Iodide → HCID 22648095, compound

Participants

Reaction Steps

A solution containing 1-(2,6 dichlorophenyl)-5-(2-chlorophenyl)-7-hydroxy-3,4-dihydro-2(1H)-quinazolinone (259 mg, 0.617 mmol) (INTERMEDIATE 49), potassium carbonate (300 mg, 2.2 mmol), allyl chloride (0.45 mL, 5.53 mmol) and sodium iodide (87 mg, 0.58 mmol) in 15 mL acetone was refluxed for seven hours. The solution was concentrated and the residue partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using 2% acetone in DCM to give 1-(2,6-dichlorophenyl)-5-(2chlorophenyl)-7-allyloxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 4.18 (d, 1H, 14.2 Hz), 4.34 (d, 1H, J=14.2 Hz), 4.40 (app d, 2H, J=5.5 Hz), 5.20-5.32(m, 2H), 5.77 (d, 1H, J=2.3 Hz), 5.82 (s, 1H), 5.90-6.00 (m, 1H), 6.44 (d, 1H, J=2.3 Hz), 7.27-7.31 (m, 1H), 7.32-7.38 (m, 3H), 7.48-7.52 (m, 3H). MS(ES) 459 (M+H); LC 1: 3.30 min.

Provenance & Evidence