Hexafluoroacetylacetone → 1-(3-Methyl-4-nitrophenyl)-3,5-bis(trifluoromethyl)-1h-pyrazole

HRID 2243263Notes

Reaction equation

HRID 2243263 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][NH2:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:13]([C:20]([C:22]([F:25])([F:24])[F:23])=O)[C:14]([C:16]([F:19])([F:18])[F:17])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[C:20]([C:22]([F:23])([F:25])[F:24])=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[N:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 73706HexafluoroacetylacetoneHCID 13158578(3-Methyl-4-nitrophenyl)hydrazine

Product 1

HCID 592103931-(3-Methyl-4-nitrophenyl)-3,5-bis(trifluoromethyl)-1h-pyrazoleYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(3-Methyl-4-nitrophenyl)-hydrazine (3.0 g) and hexafluoroacetylacetone (3.7 g) were dissolved in toluene and the solution was refluxed for 6 hours. After cooling, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (5.6 g). nD20 1.4890.

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-323fff32557c4e179db5b041f1679146
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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