2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 9842206, compound

HRID 328537Notes

Reaction equation

HRID 328537 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([C:9]2[CH2:10][CH2:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[C:14]([O:25][CH3:26])[CH:13]=3)=[O:8])=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[C:19]1([C:18]2[C:17]3[C:12](=[CH:13][C:14]([O:25][CH3:26])=[CH:15][CH:16]=3)[CH:11]=[CH:10][C:9]=2[C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18690204HCID 18690204, compound

Product 1

HCID 9842206HCID 9842206, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 11.1 g. (0.03 mole) of the product from Example 4 dissolved in benzene were added 9.0 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The mixture was refluxed for two hours and then was filtered while hot through silica, and the silica was washed three times with ethyl acetate. The ethyl acetate washings were combined with the benzene reaction mixture, and the total was concentrated to dryness. The residue was dissolved in hot methanol, and the solution was allowed to cool to obtain 4.5 g. of product. The product was recrystallized again from methanol to obtain the title compound, m.p. 122°-124° C.

Workup

  1. additionwere added 9.0 g
  2. temperatureThe mixture was refluxed for two hours
  3. filtrationwas filtered while hot through silica
  4. washthe silica was washed three times with ethyl acetate
  5. customThe ethyl acetate washings were combined with the benzene reaction mixture
  6. concentrationthe total was concentrated to dryness
  7. dissolutionThe residue was dissolved in hot methanol
  8. temperatureto cool
  9. customto obtain 4.5 g
  10. customThe product was recrystallized again from methanol

Sources & evidence

ORD record
ord-a68e9f4b9b494e94bd67e9a63bb21b70
Source dataset
uspto-grants-1977_04
Patent number
US04017546

Reaction notes

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