Water → [(1-t-butyl-1H-pyrazol-4-yl)methyl]malononitrile

HRID 2261319Notes

Reaction equation

HRID 2261319 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Cl.[C:13]([N:17]1[CH:21]=[C:20]([CH2:22]Cl)[CH:19]=[N:18]1)([CH3:16])([CH3:15])[CH3:14].O>CN(C)C=O>[C:13]([N:17]1[CH:21]=[C:20]([CH2:22][CH:2]([C:1]#[N:5])[C:3]#[N:4])[CH:19]=[N:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 687772531-tert-butyl-4-(chloromethyl)-1H-pyrazole hydrochloride

Product 1

HCID 86631044[(1-t-butyl-1H-pyrazol-4-yl)methyl]malononitrileYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.95 g of malononitrile was dissolved in 30 ml of N,N-dimethylformamide, and 12.44 g of potassium carbonate was then added under ice-cooling. Thereto a solution of 6.27 g of 1-t-butyl-4-(chloromethyl)-1H-pyrazole hydrochloride in 30 ml of N,N-dimethylformamide was added dropwise over 1 hour. After completion of the addition, the mixture was stirred at room temperature for 8 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 4.12 g of [(1-t-butyl-1H-pyrazol-4-yl)methyl]malononitrile.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition
  3. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f766dfb522174d89bff540379420eafc
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

Loading…