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

HRID 2096009Notes

Reaction equation

HRID 2096009 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-eae2d712bbb64346b9f0c103d2e49885
Source dataset
uspto-grants-2013_05
Patent number
US08449898B2

Reaction notes

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