Water → HCID 86612643, compound

HRID 1982957Notes

Reaction equation

HRID 1982957 reaction equation
Cl[CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[N:4]1.[CH2:12]([CH:15]([C:18]#[N:19])[C:16]#[N:17])[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:12]([C:15]([CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[N:4]1)([C:18]#[N:19])[C:16]#[N:17])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10931386HCID 10931386, compoundHCID 196193331-(chloromethyl)-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 86612643HCID 86612643, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.33 g of 1-(chloromethyl)-3-(trifluoromethyl)-1H-pyrazole and 0.76 g of allyl malononitrile were dissolved in 21 ml of N,N-dimethylformamide. 1.99 g of potassium carbonate was added to the solution under ice cooling with stirring, followed by stirring at room temperature for overnight. Water was added to the reaction mixture, and then extracted with MTBE. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to obtain 0.57 g of allyl {[3-(trifluoromethyl)-1H-pyrazole-1-yl]methyl}malononitrile (referred as the compound of the present invention (7), hereinafter) shown by below formula.

Workup

  1. stirringby stirring at room temperature for overnight
  2. extractionextracted with MTBE
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5bad97fbd55b4da6ae70cc1fd9bee25c
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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