2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69765333, compound

HRID 498111Notes

Reaction equation

HRID 498111 reaction equation
COC1C=CC(C[O:8][CH:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:27][O:28][CH3:29])[CH2:10][CH:11]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=[CH:13][CH2:12]2)=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.P([O-])([O-])([O-])=O>[OH:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH2:27][O:28][CH3:29])[CH2:10][CH:11]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=[CH:13][CH2:12]1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69767797HCID 69767797, compound

Product 1

HCID 69765333HCID 69765333, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6344DichloromethaneSolvent2×

Procedure

84 mg of the compound obtained in Example 29 was dissolved in a mixed solvent of 5 ml of dichloromethane and 5 ml of phosphate buffer (pH 6.8). To the resulting solution was added 0.10 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The solution was stirred at room temperature for three and a half hours. The reaction solution was diluted with dichloromethane, washed with a saturated sodium bicarbonate aqueous solution, and dried over anhydrous sodium sulfate. Then, the solvent was evaporated. The residue was purified on silica gel column, and the eluate with ethyl acetate-hexane (1:4) was collected, to afford 49 mg of the titled compound as colorless liquid.

Workup

  1. washwashed with a saturated sodium bicarbonate aqueous solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThen, the solvent was evaporated
  4. customThe residue was purified on silica gel column
  5. customthe eluate with ethyl acetate-hexane (1:4) was collected

Sources & evidence

ORD record
ord-a1adbbf777c8479dbe05b669982c3e4d
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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