Water → [(Pyridin-3-yl)methyl](3,3,3-trifluoropropyl)propanedinitrile

HRID 1795133Notes

Reaction equation

HRID 1795133 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][CH:5]([C:8]#[N:9])[C:6]#[N:7].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.O>CN(C)C=O>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][C:5]([CH2:4][CH2:3][C:2]([F:10])([F:11])[F:1])([C:8]#[N:9])[C:6]#[N:7])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 183583-(Chloromethyl)pyridineHCID 221857612-(3,3,3-Trifluoropropyl)malononitrile

Product 1

HCID 22185749[(Pyridin-3-yl)methyl](3,3,3-trifluoropropyl)propanedinitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(3,3,3-Trifluoropropyl)malononitrile (407 mg) was dissolved in N,N-dimethylformamide (5 ml), and potassium carbonate (347 mg) was added thereto, and then, a solution of 3-(chloromethyl)pyridine (320 mg) in N,N-dimethylformamide (1 ml) was added dropwise to the mixture, followed by stirring overnight at room temperature. To the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 400 mg of 2-((3-pyridyl)methyl)-2-(3,3,3-trifluoropropyl)malononitrile represented by the following formula (hereinafter referred to as the present invention compound (6)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained

Sources & evidence

ORD record
ord-6fef91e72db4407881126584aaf8a0d2
Source dataset
uspto-grants-2006_04
Patent number
US07026340B2

Reaction notes

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