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Water → [(3-cyano-1H-pyrole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrile

HRID 1982992
Notes
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Reaction equation

HRID 1982992 reaction equation
Cl[CH2:2][N:3]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4]1.[F:10][C:11]([F:20])([F:19])[CH2:12][CH2:13][CH:14]([C:17]#[N:18])[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:8]([C:5]1[CH:6]=[CH:7][N:3]([CH2:2][C:14]([CH2:13][CH2:12][C:11]([F:10])([F:19])[F:20])([C:15]#[N:16])[C:17]#[N:18])[CH:4]=1)#[N:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 231492011-chloromethyl-3-cyano-1H-pyrole

Product 1

HCID 86612675[(3-cyano-1H-pyrole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrileYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

0.27 g of 1-chloromethyl-3-cyano-1H-pyrole and 0.34 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 3ml of N,N-dimethylformamide. 0.29 g of potassium carbonate was added to the solution under ice cooling, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.37 g of [(3-cyano-1H-pyrole-1-yl) methyl] (3,3,3-trifluoropropyl) malononitrile (referred as the compound of the present invention (48), hereinafter) shown by below formula.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e61f11dca8d64fd2ad6ac3b78537587b
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07541374B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes