Thionyl Chloride → 4-Chloro-6-methyl-2-phenylquinazoline
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:6][C:5]2=O.S(Cl)([Cl:21])=O>CN(C)C=O>[Cl:21][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred slurry of 2.1 g of 6-methyl-2-phenylquinazolin-4(3H)-one and 35 ml of thionyl chloride was added dropwise 1.3 g of dimethylformamide. The mixture was maintained at reflux temperature for 90 minutes. The mixture was concentrated under reduced pressure, the residual solid was mixed with crushed ice and the washed solid collected. Two recrystallizations from petroleum ether (60°-110° fraction) gave 1.5 g of 4-chloro-6-methyl-2-phenylquinazoline, m.p. 111°-113°.