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

HRID 2043753Notes

Reaction equation

HRID 2043753 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](=O)[CH2:4][C:5](=O)[CH2:6][CH3:7].O.[NH2:13][NH2:14]>C(O)(=O)C.O>[CH2:6]([C:5]1[NH:14][N:13]=[C:3]([C:2]([F:11])([F:10])[F:1])[CH:4]=1)[CH3:7]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 678642,4-Hexanedione, 1,1,1-trifluoro-

Product 1

HCID 230062095-ethyl-3-(trifluoromethyl)-1H-pyrazoleYield 59.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A solution of 1,1,1-trifluoro-2,4-hexane-dione (2.4 g, 14.3 mmol), hydrazine hydrate (1.0 g, 19.0 mmol) and acetic acid (1 drop) in water (10 mL) was heated to reflux for 1 h. The reaction mixture was then cooled in an ice bath to form a white precipitate. The precipitate was then filtered, dissolved in chloroform and dried over MgSO4. The resulting solution was concentrated under reduced pressure to provide 1.39 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. temperatureto reflux for 1 h
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. customto form a white precipitate
  4. filtrationThe precipitate was then filtered
  5. dissolutiondissolved in chloroform
  6. dry with materialdried over MgSO4
  7. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea48f14783d245c187070bf9cebb8a9a
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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