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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19808780, compound

HRID 374016
Notes
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Reaction equation

HRID 374016 reaction equation
ClC1C=CC=CC=1Cl.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24](=[O:25])[CH:23]3[CH:18]([CH2:19][CH:20]=[C:21]4OC5C=CC=CC=5[CH:22]43)[C:17]2=[O:33])=[CH:12][CH:11]=1.C([C:36]1[C:42](=O)[C:41](Cl)=[C:40](Cl)[C:38](=[O:39])[C:37]=1C#N)#N>C(Cl)(Cl)Cl>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24](=[O:25])[C:23]34[C:37]5[CH:36]=[CH:42][CH:41]=[CH:40][C:38]=5[O:39][C:22]3=[CH:21][CH:20]=[CH:19][CH:18]4[C:17]2=[O:33])=[CH:12][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 72391,2-DichlorobenzeneHCID 19808698HCID 19808698, compound

Product 1

HCID 19808780HCID 19808780, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 ml of o-dichlorobenzene was added to a mixture of 0.50 g of 2-(4-methylphenyl)-3a,4,10b,10c-tetrahydro-1H-benzofuro[3,2-e]isoindole-1,3(2H)-dione and 0.75 g of DDQ. The mixture was refluxed for 4 hours. The reaction mixture was mixed with 50 ml of chloroform. The resulting mixture was washed with an aqueous 10% potassium carbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from methanol to obtain 0.18 g (yield: 36%) of 2-(4-methylphenyl)-1H-benzofuro-[3,2-d]isoindole-1,3(2H)-dione as light yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. washThe resulting mixture was washed with an aqueous 10% potassium carbonate solution
  3. dry with materialan aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-868dd8a3060b40bc9db3821bc615bb75
Source dataset
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05166204

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes