2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 17854617, compound

HRID 1182560Notes

Reaction equation

HRID 1182560 reaction equation
[C:1]([C:4](=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])(=O)[CH3:2].Cl.[C:33]([NH2:36])(=[NH:35])[CH3:34].C([O-])(=O)C.[Na+].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CN(C=O)C>[Cl:31][C:26]1[CH:25]=[C:24]([C:23]2[C:4]([C:5]([NH:7][CH2:8][CH2:9][CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:6])=[C:1]([CH3:2])[N:36]=[C:33]([CH3:34])[N:35]=2)[CH:29]=[CH:28][C:27]=1[Cl:30]

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone3×HCID 67170Acetamidine monohydrochlorideHCID 517045Sodium AcetateHCID 86590781HCID 86590781, compound

Product 1

HCID 17854617HCID 17854617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

120 mg (0.265 mmol) of 2-acetyl-3-(3,4-dichlorophenyl)-N-(3,3-diphenylpropyl) acrylamide was dissolved in 5 ml of DMF. 37.6 mg (0.398 mmol) of acetamidine hydrochloride and 26.1 mg of (0.318 mmol) of sodium acetate were added thereto and stirred at 100° C. overnight. After the solvent was evaporated under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in 10 ml of toluene. 120 mg (0.530 mmol) of DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone; hereinafter abbreviated as DDQ) was added thereto and stirred at 100° C. overnight. After filtration of insoluble matters and evaporation of the solvent under reduced pressure, the filtrate was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in 10 ml of toluene
  7. stirringstirred at 100° C. overnight
  8. filtrationAfter filtration of insoluble matters and evaporation of the solvent under reduced pressure
  9. additionthe filtrate was diluted with ethyl acetate
  10. washwashed with saturated aqueous sodium chloride solution
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-561635190b0345cd8ebb672cd1f6971b
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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