Trifluoroacetic acid → 5-chloro-3-(trifluoromethyl)-1H-pyrazole
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.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[NH:6][N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
In a round bottom flask with magnetic stirrer, 5-chloro-N,N-dimethyl-3-(trifluoromethyl)-1H-pyrazole-1-sulfonamide (4.38 g, 15.8 mmol) (i.e. the product of Example 13, Step B) was cooled to 0° C. and treated with trifluoroacetic acid (2.7 mL, 35 mmol). The reaction mixture was stirred at 0° C. for 1.5 h. The resulting solution was diluted with water (15 mL) and basified with sodium carbonate to pH 12. The reaction mixture was extracted with diethyl ether. The extract was dried over MgSO4 and concentrated under reduced pressure giving 2.1 g of the title compound. This compound was of sufficient purity to use in subsequent reactions.
Workup
- extractionThe reaction mixture was extracted with diethyl ether
- dry with materialThe extract was dried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3a53775e8ff74a798b0e17c1af2ca1ae
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586611B2
Reaction notes
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