Water → N-[2-(hydroxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](Cl)=[O:8])[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3]1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][OH:22].C(N(CC)CC)C.O>O1CCCC1>[OH:22][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:7]([C:5]1[C:4]([C:10]([F:13])([F:12])[F:11])=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 34.5 g (0.16 mols) 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl chloride in 50 ml tetrahydrofuran is added dropwise at room temperature to a solution of 20.0 g (0.16 mols) 2-aminophenylmethanol and 36 ml (0.26 mols) triethylamine in 250 ml tetrahydrofuran. After the exotherm has subsided, the reaction is refluxed for 6 hours, then stirred at room temperature for another 48 hours. The reaction mixture is added to about 250 ml water, extracted with ethyl acetate, washed with 2 N hydrochloric acid gewaschen, dried over magnesium sulfate and concentrated tinder vacuum. Column chromatography (gradient cyclohexane/ethyl acetate) yielded 33.8 g (69% theoretical yield) of N-[2-(hydroxymethyl)phenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide [logP (pH 2.3)=1.55].
Workup
- temperaturethe reaction is refluxed for 6 hours
- extractionextracted with ethyl acetate
- washwashed with 2 N hydrochloric acid gewaschen
- dry with materialdried over magnesium sulfate
- concentrationconcentrated tinder vacuum
Sources & evidence
- ORD record
- ord-8b53106cebc6443eb797c5da890a20b4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842710B2
Reaction notes
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