Methylhydrazine → 3-(2,5-difluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

HRID 260940Notes

Reaction equation

HRID 260940 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]([C:13]([F:16])([F:15])[F:14])=O.[CH3:18][NH:19][NH2:20]>C(O)(=O)C.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:19]([CH3:18])[N:20]=1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 152785581-(2,5-Difluorophenyl)-4,4,4-trifluorobutane-1,3-dione

Product 1

HCID 152785593-(2,5-difluorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

34.5 g of 1-(2,5-difluorophenyl)-3-(trifluoromethyl)-propane-1,3-dione was dissolved in 250 ml of acetic acid and 9.5 mL of methylhydrazine slowly added. The mixture was heated at 100° C. for 5 minutes then cooled and diluted with ether. The ether solution was washed with water and potassium carbonate solution, then dried with magnesium sulfate, filtered and concentrated. The residue was chromatographed to give 9.5 g of 3-(2,5-difluorophenyl)-1-methyl-5-(trifluoro-methyl)-1H-pyrazole.

Workup

  1. temperaturethen cooled
  2. washThe ether solution was washed with water and potassium carbonate solution
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-e353ecbcc9f8498f82cad045ce05e992
Source dataset
uspto-grants-1996_06
Patent number
US05530126

Reaction notes

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