2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4(3h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-8-methoxy-3-(4-methoxyphenyl)-
Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:19](=[O:29])[C:18]3[C:13](=[C:14]([O:30][CH3:31])[CH:15]=[CH:16][CH:17]=3)[NH:12]2)=[CH:7][CH:6]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:19](=[O:29])[C:18]3[C:13](=[C:14]([O:30][CH3:31])[CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 18.0 g (0.0410 mol) of 2-[4-(2-chloro-ethoxy)-phenyl]-8-methoxy-3-(4-methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one in 500 mL of toluene was added 9.31 g (0.0410 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The reaction mixture was stirred and heated under reflux for 3 hours. After cooling to room temperature, the solvent was removed in a rotary evaporator. Ethanol (300 mL) was added to the crude product and stirred at room temperature overnight. The precipitate was collected by vacuum filtration. An analytical sample (mp 151-152° C.) was obtained by recrystallization from ethanol.