2-(Methylamino)ethanol → 2-{Methyl[2-nitro-4-(trifluoromethyl)phenyl]amino}ethan-1-ol
Reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][N:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH2:3][CH2:4][OH:5]Participants
Procedure
2-(Methylamino)ethanol (17.3 g, 231 mmol) was added dropwise to a solution of 4-chloro-3-nitrobenzotrifluoride (26.0 g, 115 mmol) in N,N-dimethylformamide (100 ml) at 0° C. After the reaction temperature was raised to room temperature, the reaction mixture was stirred at room temperature for 1 hour, poured into a saturated aqueous ammonium chloride solution, and then extracted twice with ethyl acetate. The organic layer was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=97/3) to obtain an oil of 4-[N-methyl-N-(2-hydroxyethyl)amino]-3-nitrobenzotrifluoride.
Workup
- extractionextracted twice with ethyl acetate
- washThe organic layer was washed with a 5% aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=97/3)
Sources & evidence
- ORD record
- ord-f3fe193014bb43a9a49003200b9968cd
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271251B1
Reaction notes
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