Formaldehyde → [3-(Trifluoromethyl)-1H-pyrazol-1-yl]methyl 4-methylbenzenesulfonate
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[H-].[Na+].[CH2:12]=[O:13].C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(OCC)(=O)C.O.CN(C)C=O>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:13][CH2:12][N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To an N,N-dimethylformamide solution (2 mL) of 3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.73 mmol), sodium hydride (35.3 mg, 0.88 mmol, purity 55%) was added at room temperature and the resultant solution was stirred for 1 hour. To the reaction solution, paraformaldehyde (26.4 mg, 0.88 mmol) was added and the resultant mixture was stirred for 1 day. Subsequently, triethylamine (204 μL, 1.46 mmol) and p-toluenesulfonyl chloride (230 mg, 1.21 mmol) were added at 0° C. to the reaction solution and the resultant mixture was stirred for 40 minutes. After completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (181 mg, yield 78%).
Workup
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f206a2e858e8400c8f8347ef0cc42152
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403798B2
Reaction notes
Loading…