Water → [(3-t-butyl-1H-1,2,4-triazole-1-yl)methyl](3,3,3-trifluoropropyl) malononitrile

HRID 1982974Notes

Reaction equation

HRID 1982974 reaction equation
Cl.[C:2]([C:6]1[N:10]=[CH:9][N:8]([CH2:11]Cl)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].[F:13][C:14]([F:23])([F:22])[CH2:15][CH2:16][CH:17]([C:20]#[N:21])[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:2]([C:6]1[N:10]=[CH:9][N:8]([CH2:11][C:17]([CH2:16][CH2:15][C:14]([F:13])([F:22])[F:23])([C:18]#[N:19])[C:20]#[N:21])[N:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 231491201-(chloromethyl)-3-t-butyl-1H-1,2,4-triazole hydrochloride

Product 1

HCID 86612660[(3-t-butyl-1H-1,2,4-triazole-1-yl)methyl](3,3,3-trifluoropropyl) malononitrileYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.61 g of 3-t-butyl-1-(chloromethyl)-1H-1,2,4-triazole hydrochloride and 1.24 g of (3,3,3-trifluoropropyl) malononitrile were dissolved in 22 ml of N,N-dimethylformamide. 2.13 g of potassium carbonate was added to the solution under ice cooling with stirring, followed by stirring at room temperature for 4 hours. 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 recrystallized from hexane-MTBE to obtain 0.77 g of [(3-t-butyl-1H-1,2,4-triazole-1-yl)methyl](3,3,3-trifluoropropyl) malononitrile (referred as the compound of the present invention (29), hereinafter) shown by below formula.

Workup

  1. stirringby stirring at room temperature for 4 hours
  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. customThe residue was recrystallized from hexane-MTBE

Sources & evidence

ORD record
ord-77ddb20e53c340e1afd9a5d113a4e75d
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

Loading…