2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-[4-(2-Chloro-ethoxy)-phenyl]-7-methoxy-2-(4-methoxy-phenyl)-3H-quinazolin-4-one

HRID 617124Notes

Reaction equation

HRID 617124 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[CH:17][CH:18]=3)[NH:13][CH:12]2[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=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]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 218510803-[4-(2-chloro-ethoxy)-phenyl]-7-methoxy-2-(4methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one

Product 1

HCID 218510823-[4-(2-Chloro-ethoxy)-phenyl]-7-methoxy-2-(4-methoxy-phenyl)-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8.1 g (0.0185 mol) of 3-[4-(2-chloro-ethoxy)-phenyl]-7-methoxy-2-(4methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one in 300 mL of toluene was added 4.2 g (0.0185 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The reaction mixture was stirred and heated to reflux for 2 hours. The toluene was removed in a rotary evaporator. Ethanol (300 mL) was added to the reaction flask which was allowed to stir at room temperature overnight. The precipitate was collected by vacuum filtration and amounted to 6.9 g. The product (mp 186-187° C.) was used in the next step without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe toluene was removed in a rotary evaporator
  4. additionEthanol (300 mL) was added to the reaction flask which
  5. stirringto stir at room temperature overnight
  6. filtrationThe precipitate was collected by vacuum filtration
  7. customThe product (mp 186-187° C.) was used in the next step without further purification

Sources & evidence

ORD record
ord-12d5ef3893d249eab44ce3cbcbe16c21
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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