4-(Trifluoromethyl)aniline → N-[(1-methyl-1H-pyrazol-5-yl)methyl]-4-(trifluoromethyl)aniline
Reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][CH:4]=[N:3]1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:1][N:2]1[C:6]([CH2:7][NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[CH:5][CH:4]=[N:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Acetic acid (0.87 mL) was added to a chloroform (10 mL) solution that contained 1-methyl-1H-pyrazol-5-carbaldehyde (1.00 g) and 4-aminobenzotrifluoride (1.76 g) at a room temperature, and the obtained solution was then stirred for 10 minutes. Thereafter, sodium triacetoxyborohydride (2.89 g) was added to the reaction solution, and the obtained mixture was then stirred for 5.5 hours. Thereafter, a saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The obtained solid was washed with diisopropyl ether, so as to obtain the title compound (1.88 g) in the form of a light yellow solid.
Workup
- customat a room temperature
- stirringthe obtained mixture was then stirred for 5.5 hours
- extractionthe obtained mixture was then extracted with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationwas then concentrated under a reduced pressure
- washThe obtained solid was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-e133bff63447443d85dfacbcf0991cf7
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642626B2
Reaction notes
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