2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 18422136, compound

HRID 649968Notes

Reaction equation

HRID 649968 reaction equation
[CH2:1]1[C:6]2[C:7]3[C:13](=[O:14])[NH:12][C:11]4[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=4[O:9][C:8]=3[S:19][C:5]=2[CH2:4][CH2:3][CH2:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH:1]1[C:6]2[C:7]3[C:13](=[O:14])[NH:12][C:11]4[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=4[O:9][C:8]=3[S:19][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18422160HCID 18422160, compound

Product 1

HCID 18422136HCID 18422136, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1,2,3,4-Tetrahydro-[1]benzothieno[2,3-b][1,5]benzoxazepin-12(11H)-one (1.5 g) and dichlorodicyano-p-benzoquinone (2.6 g) was dissolved in benzene (45 ml) and the mixture was stirred under reflux with heating for 12 hours. The reaction mixture was evaporated under reduced pressure to remove the solvent, and the residue was added to a mixture of chloroform/water. The organic layer was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform) to give [1]benzothieno[2,3-b][1,5]benzoxazepin-12(11H)-one (1.25 g).

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 12 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customto remove the solvent
  5. additionthe residue was added to a mixture of chloroform/water
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-0056e7ee99614033aabee62670b76f5c
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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