Thionyl Chloride → 4-Chloro-2-(4-chlorophenyl)-6,7-dimethoxyquinazoline
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:17][C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([O:19][CH3:20])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>CN(C=O)C>[Cl:25][C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([O:19][CH3:20])[CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 2-(4-chlorophenyl)-6,7-dimethoxyquinazolin-4(3H)-one (200 mg), thionyl chloride (10 mL) and DMF (0.3 mL) was refluxed for 2 h. Solvents were removed under vacuum. The mixture was poured into ice cold water and stirred for 10 min. The solution was basified with ammonia and stirred for 5 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the product as an yellow color solid (180 mg, 86%), mp 204-206° C. 1H NMR (400 MHz, DMSO-d6): δ 8.47 (2H, d, J=8.4 Hz), 7.66 (2H, d, J=8.4 Hz), 7.52 (1H, s), 7.44 (1H, s), 4.08 (3H, s), 4.05 (3H, s).