2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4(3h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-8-methoxy-3-(4-methoxyphenyl)-

HRID 617130Notes

Reaction equation

HRID 617130 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]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 218510814(1h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-2,3-dihydro-8-methoxy-3-(4-methoxyphenyl)-

Product 1

HCID 158708824(3h)-Quinazolinone,2-[4-(2-chloroethoxy)phenyl]-8-methoxy-3-(4-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customthe solvent was removed in a rotary evaporator
  4. additionEthanol (300 mL) was added to the crude product
  5. stirringstirred at room temperature overnight
  6. filtrationThe precipitate was collected by vacuum filtration
  7. customAn analytical sample (mp 151-152° C.) was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-868fe2344e1946bfabbf3ff10befefe9
Source dataset
uspto-grants-1999_09
Patent number
US05948775

Reaction notes

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