Water → HCID 86760868, compound

HRID 1982971Notes

Reaction equation

HRID 1982971 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.[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]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:4]1)([C:18]#[N:19])[C:16]#[N:17])[CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7017727methyl 1-(chloromethyl)-1H-pyrazole-4-carboxylateHCID 10931386HCID 10931386, compound

Product 1

HCID 86760868HCID 86760868, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.79 g of 1-(chloromethyl)-4-methoxycarbonyl-1H-pyrazole and 0.49 g of allyl malononitrile were dissolved in 15 ml of N,N-dimethylformamide. 1.26 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 0.50 g of allyl [{4-(methoxycarbonyl)-1H-pyrazole-1-yl}methyl]malononitrile (referred to as the compound of the present invention (24), 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-271914447b094c99a1d18c0b685a180f
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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