Water → HCID 86612641, compound

HRID 1982955Notes

Reaction equation

HRID 1982955 reaction equation
Cl.Cl[CH2:3][N:4]1[CH:8]=[C:7]2[CH2:9][CH2:10][C:11]([CH3:13])([CH3:12])[C:6]2=[N:5]1.[F:14][C:15]([F:24])([F:23])[CH2:16][CH2:17][CH:18]([C:21]#[N:22])[C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:12][C:11]1([CH3:13])[C:6]2=[N:5][N:4]([CH2:3][C:18]([CH2:17][CH2:16][C:15]([F:14])([F:23])[F:24])([C:19]#[N:20])[C:21]#[N:22])[CH:8]=[C:7]2[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 67309262HCID 67309262, compound

Product 1

HCID 86612641HCID 86612641, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.58 g of 2-(chloromethyl)-6,6-dimethyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole hydrochloride and 0.43 g of (3,3,3-trifluoropropyl) malononitrile were dissolved in 8 ml of N,N-dimethylformamide. 0.73 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 0.27 g of [(6,6-dimethyl-5,6-dihydro-cyclopenta[c]pyrazole-2(4H)-yl)methyl](3,3,3-trifluoropropyl) malononitrile (referred as the compound of the present invention (5), 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-affb3fb552e44593b8c142349f22a678
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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