2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19849123, compound

HRID 1608319Notes

Reaction equation

HRID 1608319 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH2:15]([O:17][C:18]([CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH2:28][NH:27]2)=[O:19])[CH3:16]>C1C=CC=CC=1>[CH2:15]([O:17][C:18]([CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH:28]=[N:27]2)=[O:19])[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15051872HCID 15051872, compound

Product 1

HCID 19849123HCID 19849123, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Dichlorodicyanobenzoquinone (DDQ) 4.5 g (19.8 mM) was added to the compound 925 5 g (18 mM) dissolved in benzene 300 ml with heating, and the mixture was refluxed for 3 hours. The reaction mixture was filtered hot and then the filtrate was concentrated in vacuo. The residue, dissolved in chloroform, was washed with water, dried by adding anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica gel (C-200) packed with chloroform, and purified by eluting with chloroform-methanol (300:1), (200:1) and (100:1), in this order to obtain the compound 914 as colorless crystals.

Workup

  1. temperaturewith heating
  2. temperaturethe mixture was refluxed for 3 hours
  3. filtrationThe reaction mixture was filtered hot
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue, dissolved in chloroform
  6. washwas washed with water
  7. customdried
  8. additionby adding anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. additionThe residue was charged on a column of silica gel (C-200)
  11. custompurified
  12. washby eluting with chloroform-methanol (300:1), (200:1) and (100:1), in this order

Sources & evidence

ORD record
ord-c0feb53fc3ad4846a5b3a94e259f8a4e
Source dataset
uspto-grants-1989_09
Patent number
US04870175

Reaction notes

Loading…