Water → [{4-(methoxycarbonyl)-1H-pyrazole-1-yl}methyl](3,3,3-trifluoropropyl) malononitrile

HRID 1982970Notes

Reaction equation

HRID 1982970 reaction equation
Cl[CH2:2][N:3]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:4]1.[F:12][C:13]([F:22])([F:21])[CH2:14][CH2:15][CH:16]([C:19]#[N:20])[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[N:4][N:3]([CH2:2][C:16]([CH2:15][CH2:14][C:13]([F:12])([F:21])[F:22])([C:17]#[N:18])[C:19]#[N:20])[CH:7]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7017727methyl 1-(chloromethyl)-1H-pyrazole-4-carboxylateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrile

Product 1

HCID 86760867[{4-(methoxycarbonyl)-1H-pyrazole-1-yl}methyl](3,3,3-trifluoropropyl) malononitrileYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.80 g of 1-(chloromethyl)-4-methoxycarbonyl-1H-pyrazole and 0.75 g of (3,3,3-trifluoropropyl) malononitrile were dissolved in 15 ml of N,N-dimethylformamide. 1.27 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 subjected to silica gel column chromatography, and then recrystallized from hexane-chloroform to obtain 0.48 g of [{4-(methoxycarbonyl)-1H-pyrazole-1-yl}methyl](3,3,3-trifluoropropyl) malononitrile (referred to as the compound of the present invention (23), 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. customrecrystallized from hexane-chloroform

Sources & evidence

ORD record
ord-69506cd6b53c46bfaabaff924507ed72
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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