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

HRID 1982966Notes

Reaction equation

HRID 1982966 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][N:6]([CH2:8]Cl)[CH:7]=1.[F:10][C:11]([F:20])([F:19])[CH2:12][CH2:13][CH:14]([C:17]#[N:18])[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[N:5][N:6]([CH2:8][C:14]([CH2:13][CH2:12][C:11]([F:10])([F:19])[F:20])([C:15]#[N:16])[C:17]#[N:18])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 231491194-chloro-1-(chloromethyl)-1H-pyrazole hydrochloride

Product 1

HCID 86612654[(4-chloro-1H-pyrazole-1-yl)methyl](3,3,3-trifluoropropyl) malononitrileYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.44 g of 4-chloro-1-(chloromethyl)-1H-pyrazole hydrochloride and 1.56 g of (3,3,3-trifluoropropyl) malononitrile were dissolved in 30 ml of N,N-dimethylformamide. 2.76 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 to obtain 1.73 g of [(4-chloro-1H-pyrazole-1-yl)methyl](3,3,3-trifluoropropyl) malononitrile (referred as the compound of the present invention (19), 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

Sources & evidence

ORD record
ord-687234ebd08349bd86cbf177e39638be
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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