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

HRID 2395632Notes

Reaction equation

HRID 2395632 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-371886b109dc4d35ae8b5992a3d06102
Source dataset
uspto-grants-1996_02
Patent number
US05489571

Reaction notes

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