2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 15870885, compound

HRID 617131Notes

Reaction equation

HRID 617131 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](=[C:15]([O:22][CH3:23])[CH:16]=[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](=[C:15]([O:22][CH3:23])[CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15870884HCID 15870884, compound

Product 1

HCID 15870885HCID 15870885, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 17.28 g (0.0394 mol) of 3-[4-(2-chloro-ethoxy)-phenyl]-8-methoxy-2-(4-methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one in 300 mL of toluene was added 8.94 g (0.0394 mol) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The reaction mixture was stirred and heated to reflux for 3 hours. The toluene then was removed in a rotary evaporator. Methanol (300 mL) was added to the reaction flask which was allowed to stir at room temperature overnight. The precipitate (mp 209-211° C.) was collected by vacuum filtration and amounted to 15.8 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe toluene then was removed in a rotary evaporator
  4. additionMethanol (300 mL) was added to the reaction flask which
  5. stirringto stir at room temperature overnight
  6. filtrationThe precipitate (mp 209-211° C.) was collected by vacuum filtration

Sources & evidence

ORD record
ord-17641b3ce9c44d52a38cb79b39dabb59
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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