2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 10499269, compound

HRID 1761969Notes

Reaction equation

HRID 1761969 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[S:25][CH:24]([CH:33]([CH3:35])[CH3:34])[C:23]=2[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:18][CH:17]=1>C(Cl)Cl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:24]([CH:33]([CH3:35])[CH3:34])[S:25][C:26]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10714229HCID 10714229, compound

Product 1

HCID 10499269HCID 10499269, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 25 g of 2,3 dichloro-5,6-dicyanobenzoquinone in 1 liter of methylene chloride at room temperature was added slowly a solution of 40 g of the dihydrothiophene carboxylate of Step 5, above, in 125 ml of methylene chloride. The mixture was stirred at room temperature for 24 hours, filtered, and the filtrate was washed with 10% aqueous sodium bicarbonate solution. The organic phase was separated and the solvent was removed under reduced pressure. The residue was filtered through a pad of silica gel to remove any polar material. Evaporation of the solvent gave 41.5 g of the title product of this preparation.

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed with 10% aqueous sodium bicarbonate solution
  3. customThe organic phase was separated
  4. customthe solvent was removed under reduced pressure
  5. filtrationThe residue was filtered through a pad of silica gel
  6. customto remove any polar material
  7. customEvaporation of the solvent
  8. customgave

Sources & evidence

ORD record
ord-bd61afef1e884599b5990780e563fa03
Source dataset
uspto-grants-1989_05
Patent number
US04829081

Reaction notes

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