2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21196575, compound

HRID 1066883Notes

Reaction equation

HRID 1066883 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:13]3[CH:15]=[CH:16][S:17][C:12]=3[CH2:11][CH2:10][C:9]=2[CH:8]=[N:7]1)=[N+:2]=[N-:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[N:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]3[S:17][CH:16]=[CH:15][C:13]3=2)[CH:8]=[N:7]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 21196682HCID 21196682, compound

Product 1

HCID 21196575HCID 21196575, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.00 g of 1-(2-azidoethyl)-4,5-dihydro-1H-thieno[2,3-g]indazole was dissolved in 30 ml of dioxane, 2.80 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added at room temperature, and the mixture was heated under reflux for 8 hours. The reaction mixture was cooled, poured into sodium bicarbonate aqueous solution and then extracted with chloroform. The organic layers were combined and dried with anhydrous magnesium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography to give 0.73 g of 1-(2-azidoethyl)-1H-thieno[2,3-g]indazole as a pale brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with chloroform
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe solvent was concentrated under a reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-64bbe581bc904174b77acd4374c3f32a
Source dataset
uspto-grants-2001_06
Patent number
US06245796B1

Reaction notes

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