Water → HCID 86612650, compound

HRID 1982964Notes

Reaction equation

HRID 1982964 reaction equation
Cl.[Br:2][C:3]1[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:5][N:6]([CH2:8]Cl)[CH:7]=1.[CH2:14]([CH:17]([C:20]#[N:21])[C:18]#[N:19])[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:14]([C:17]([CH2:8][N:6]1[CH:7]=[C:3]([Br:2])[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])=[N:5]1)([C:20]#[N:21])[C:18]#[N:19])[CH:15]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10931386HCID 10931386, compoundHCID 231491914-bromo-3-t-butyl-1-(chloromethyl)-1H-pyrazole hydrochloride

Product 1

HCID 86612650HCID 86612650, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.84 g of 4-bromo-3-t-butyl-1-(chloromethyl)-1H-pyrazole hydrochloride and 0.77 g of allyl malononitrile were dissolved in 21 ml of N,N-dimethylformamide. 2.02 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 0.84 g of allyl [(4-bromo-3-t-butyl-1H-pyrazole-1-yl)methyl]malononitrile (referred as the compound of the present invention (14), 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-68a1b6c463df4f6f9d92f9a28433ace6
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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