Water → 1-(3-methyl-4-nitrobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole

HRID 2243244Notes

Reaction equation

HRID 2243244 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[NH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][N:16]1[C:15]([C:14]([F:13])([F:25])[F:24])=[CH:19][C:18]([C:20]([F:21])([F:22])[F:23])=[N:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 5189913,5-Bis(trifluoromethyl)pyrazole

Product 1

HCID 592104091-(3-methyl-4-nitrobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazoleYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-4-nitrobenzyl chloride (1.81 g), 3,5-bis(trifluoromethyl)-1H-pyrazole (2.0 g) and potassium carbonate (1.63 g) were stirred in DMF (20 ml) at 60° C. for 1 hour. After finishing the reaction, water (100 ml) was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride (100 ml) and dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrobenzyl)-3,5-bis-(trifluoromethyl)-1H-pyrazole (3.3 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride (100 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a22a4be0f9647218a4049ad69acef08
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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