Trifluoroacetic acid → 5-chloro-3-(trifluoromethyl)-1H-pyrazole

HRID 238673Notes

Reaction equation

HRID 238673 reaction equation
[Cl:1][C:2]1[N:6](S(N(C)C)(=O)=O)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.FC(F)(F)C(O)=O>O.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[NH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674628085-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide2×

Product 1

HCID 1785061975-chloro-3-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (i.e. the product of Example 10, Step B) (4.38 g, 15.8 mmol) and trifluoroacetic acid (2.7 mL, 35 mmol) was stirred at 0° C. for 1.5 h. The reaction mixture was diluted with water (15 mL), and sodium carbonate was added to raise the pH to 12. The solution was extracted with diethyl ether, dried (MgSO4), and concentrated under reduced pressure to give 2.1 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. additionwas added
  2. temperatureto raise the pH to 12
  3. extractionThe solution was extracted with diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cede304086f944cc80ebed391f7dfdf4
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

Loading…