2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19903339, compound

HRID 2372385Notes

Reaction equation

HRID 2372385 reaction equation
[CH3:1][NH:2][C:3](=[O:20])[CH2:4][CH:5]1[CH2:9][S:8][C:7]2=[C:10]([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:11]([CH3:13])[CH2:12][N:6]12.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)(Cl)Cl>[CH3:1][NH:2][C:3](=[O:20])[CH2:4][CH:5]1[CH2:9][S:8][C:7]2=[C:10]([C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[O:15])[C:11]([CH3:13])=[CH:12][N:6]12

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19903332HCID 19903332, compound

Product 1

HCID 19903339HCID 19903339, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.1 g of N-methyl-(7-isopropoxycarbonyl-6-methyl-2,3,5,6- tetrahydropyrrolo[2,1-b]-thiazol-3-yl)acetamide was dissolved in 150 ml of chloroform and 3.9 g of 2,3-dicyano-5,6-dichloro-parabenzoquinone was added thereto under ice-cooling and stirring. The mixture was stirred at room temperature for 1 hour. After removing the insoluble matters, the chloroform layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride. After drying over anhydrous sodium sulfate and distilling off the solvent, the obtained residue was purified by silica gel column chromatography. Thus 2.0 g of the title compound was obtained.

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customAfter removing the insoluble matters
  4. washthe chloroform layer was successively washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. distillationdistilling off the solvent
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ccc96bcfa65e49aa9fafa5b395f6f7d3
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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