Hydrazine → 5-ethyl-3-(trifluoromethyl)-1H-pyrazole

HRID 270783Notes

Reaction equation

HRID 270783 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](=O)[CH2:4][C:5](=O)[CH2:6][CH3:7].[NH2:12][NH2:13]>C(O)C>[CH2:6]([C:5]1[NH:13][N:12]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=1)[CH3:7]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 678642,4-Hexanedione, 1,1,1-trifluoro-

Product 1

HCID 230062095-ethyl-3-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1,1-Trifluoro-hexane-2,4-dione (1 g, 5.95 mmol) in absolute ethanol (10 mL) was added NH2NH2.xH2O drop-wise at 0° C. The reaction mixture warmed to the room temperature during 1 hour and refluxed overnight. Ethanol was then evaporated, residue dissolved in ethyl acetate (20 mL), washed consecutively with saturated brine solution and water, dried with Na2SO4 and concentrated to give the title compound as colorless oil.

Workup

  1. customat 0° C
  2. temperaturerefluxed overnight
  3. customEthanol was then evaporated
  4. dissolutionresidue dissolved in ethyl acetate (20 mL)
  5. washwashed consecutively with saturated brine solution and water
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9579df4aa4e44657ac874cab1968398c
Source dataset
uspto-grants-2008_11
Patent number
US07449576B1

Reaction notes

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