2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89739681, compound

HRID 1521800Notes

Reaction equation

HRID 1521800 reaction equation
[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH:9]=[CH:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 123269771,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)

Product 1

HCID 89739681HCID 89739681, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 1,1′-(4,5-dihydronaphtho[1,2-b]thiophene-2,7-diyl))diethanone (5c) (1 g, 3.7 mmol) in 30 ml of toluene, DDQ (0.84 g, 3.7 mmol) was added and the mixture was stirred at 110° C. for 60 hr. The reaction mixture was concentrated under reduced pressure, 100 ml water was added and the organics were extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography to obtain 1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)diethanone as a brown solid (10a) (0.45 g, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 100 ml water
  2. additionwas added
  3. extractionthe organics were extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude compound which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e6f76e7971904a48b97accfc62652a67
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

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