Dichloromethane → 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid
Reaction equation
NC1C(C)=CC(Cl)=CC=1C(NC)=[O:5].ClCCl.[Cl:17][C:18]1[C:19]([N:25]2[C:29]([C:30](Cl)=[O:31])=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[N:26]2)=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=1.C(N(CC)CC)C>O>[Cl:17][C:18]1[C:19]([N:25]2[C:29]([C:30]([OH:5])=[O:31])=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[N:26]2)=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 100 mL flask, 2-amino-5-chloro-N,3-dimethylbenzamide (0.24 g, 1.22 mmol), dichloromethane (20 mL), 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride (0.42 g, 1.22 mmol) and triethylamine (0.12 g, 1.22 mmol) were added sequentially. The reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was washed with saturated sodium carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the compound 3 (0.50 g) as a white solid in 81% yield.
Workup
- extractionextracted with ethyl acetate (2×100 mL)
- washThe organic layer was washed with saturated sodium carbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-188a25dbdbdc452aa410993f078f369f
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492409B2
Reaction notes
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