Water → HCID 86612674, compound

HRID 1982991Notes

Reaction equation

HRID 1982991 reaction equation
Cl[CH2:2][N:3]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4]1.[F:17][C:18]([F:27])([F:26])[CH2:19][CH2:20][CH:21]([C:24]#[N:25])[C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:15]([O:14][C:12]([C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][N:3]([CH2:2][C:21]([CH2:20][CH2:19][C:18]([F:17])([F:26])[F:27])([C:22]#[N:23])[C:24]#[N:25])[CH:4]=1)=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 221857612-(3,3,3-Trifluoropropyl)malononitrileHCID 23149199HCID 23149199, compound

Product 1

HCID 86612674HCID 86612674, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.23 g of 1-chloromethyl-4-trifluoromethyl-3-ethoxycarbonyl-1H-pyrole and 0.15 g of (3,3,3-trifluoropropyl)malononitrile were dissolved in 2 ml of N,N-dimethylformamide. 0.13 g of potassium carbonate was added to the solution under ice cooling, followed by stirring at room temperature for overnight. 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 0.20 g of [(3-ethoxycarbonyl-4-trifluoromethyl-1H-pyrole-1-yl)methyl](3,3,3-trifluoropropyl)malononitrile (referred as the compound of the present invention (47), 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-85f42c412eb74730aca63f93dc8cbfad
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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