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

HRID 1982976Notes

Reaction equation

HRID 1982976 reaction equation
Cl.Cl[CH2:3][N:4]1[CH:8]=[N:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:5]1.[CH2:13]([CH:16]([C:19]#[N:20])[C:17]#[N:18])[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([C:16]([CH2:3][N:4]1[CH:8]=[N:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:5]1)([C:19]#[N:20])[C:17]#[N:18])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10931386HCID 10931386, compoundHCID 231491201-(chloromethyl)-3-t-butyl-1H-1,2,4-triazole hydrochloride

Product 1

HCID 86612662allyl [(3-t-butyl-1H-1,2,4-triazole-1-yl)methyl]malononitrileYield 10.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.28 g of 1-(chloromethyl)-3-t-butyl-1H-1,2,4-triazole hydrochloride and 0.77 g of allyl malononitrile were dissolved in 21 ml of N,N-dimethylformamide. 1.01 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 0.16 g of allyl [(3-t-butyl-1H-1,2,4-triazole-1-yl)methyl]malononitrile (referred as the compound of the present invention (31), 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-07a248ec83934a36b6b7741210cbeb8e
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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