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

HRID 1198399Notes

Reaction equation

HRID 1198399 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-a1144cefd6504c70a927c59c044195c6
Source dataset
uspto-grants-1994_01
Patent number
US05281571

Reaction notes

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