Water → HCID 12090224, compound

HRID 353206Notes

Reaction equation

HRID 353206 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[H-].[Na+].F[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:21][C:22]2[N:26]([CH3:27])[N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:20]=1)[C:16]#[N:17].O>CC(N(C)C)=O>[CH3:27][N:26]1[C:22]([O:21][C:19]2[CH:18]=[C:15]([CH:14]=[C:13]([N:5]3[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]3)[CH:20]=2)[C:16]#[N:17])=[CH:23][C:24]([C:28]([F:31])([F:30])[F:29])=[N:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 18070343-(Trifluoromethyl)pyrazoleHCID 12090222HCID 12090222, compound

Product 1

HCID 12090224HCID 12090224, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Under an atmosphere of nitrogen, 0.131 g (0.96 mmol) of 3-trifluoromethylpyrazole was initially charged in 5 ml of dimethylacetamide, and 0.033 g (1.1 mmol) of sodium hydride (80%) was added at 0° C. The mixture was allowed to warm to room temperature, and 0.250 g (0.88 mmol) of 3-fluoro-5-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)benzonitrile was added, the mixture was heated at 140° C. for 8 h and cooled to room temperature, water was added to the reaction solution and the solution was stirred for a number of minutes. The mixture was extracted twice with heptane/ethyl acetate (1:1) and twice with ethyl acetate. The combined phases were washed with water and then dried over magnesium sulfate, filtered and concentrated. Column chromatography of the crude product gave 0.240 g of 3-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-(3-trifluoromethylpyrazol-1-yl)benzonitrile in the form of white crystals of melting point of 116-117° C.

Workup

  1. temperaturethe mixture was heated at 140° C. for 8 h
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted twice with heptane/ethyl acetate (1:1) and twice with ethyl acetate
  4. washThe combined phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b4317f20d545ffbbd45024bf528caa
Source dataset
uspto-grants-2004_06
Patent number
US06750222B2

Reaction notes

Loading…