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

HRID 1281839Notes

Reaction equation

HRID 1281839 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-2bd7934eaaea407897d4c271d3b6d318
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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