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Water → N-(3-cyano-2,4-difluorophenyl)-N,1-dimethyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500063
Notes
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Reaction equation

HRID 1500063 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[C:9]([C:11]1[C:12]([F:38])=[C:13]([NH:18][C:19]([C:21]2[N:25]([CH3:26])[N:24]=[C:23]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])[C:22]=2[C:34]([F:37])([F:36])[F:35])=[O:20])[CH:14]=[CH:15][C:16]=1[F:17])#[N:10].O>CN(C=O)C>[C:9]([C:11]1[C:12]([F:38])=[C:13]([N:18]([CH3:1])[C:19]([C:21]2[N:25]([CH3:26])[N:24]=[C:23]([C:27]([F:32])([F:33])[C:28]([F:31])([F:30])[F:29])[C:22]=2[C:34]([F:36])([F:37])[F:35])=[O:20])[CH:14]=[CH:15][C:16]=1[F:17])#[N:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89651058N-(3-cyano-2,4-difluorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Product 1

HCID 89650683N-(3-cyano-2,4-difluorophenyl)-N,1-dimethyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.28 g, 5.58 mmol, 2.0 eq.) and iodomethane (0.5 ml, 1.2 g, 8.4 mmol, 3.0 eq.) were added to a solution of N-(3-cyano-2,4-difluorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (1.25 g, 2.79 mmol) in DMF (4 ml). After 5 h, water was added, the mixture was extracted with ethyl acetate and the extract was washed with sat. aq. sodium chloride solution and dried over MgSO4. Filtration through silica gel gave N-(3-cyano-2,4-difluorophenyl)-N,1-dimethyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (1.27 g, 98%) as a mixture of rotamers which was reacted further without additional purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with sat. aq. sodium chloride solution
  3. dry with materialdried over MgSO4
  4. filtrationFiltration through silica gel

Sources & evidence

ORD record
ord-8c1b14c2b18546a8b0e399acc3b5075a
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09204645B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes