1,2-Dichloroethane → N-methoxy-N-methyl-2-[3-(trifluoromethyl)phenyl]acetamide
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[F:6][C:7]([F:19])([F:18])[C:8]1[CH:9]=[C:10]([CH2:14][C:15](O)=[O:16])[CH:11]=[CH:12][CH:13]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[CH3:5][O:4][N:3]([CH3:2])[C:15](=[O:16])[CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:7]([F:19])([F:18])[F:6])[CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of N,O-dimethylhydroxylamine hydrochloride (1.577 g, 16.2 mmol) in DMF (25 mL) and CH2Cl2 (25 mL) at 0° C. was added triethylamine (2.25 mL). After stirring for 5 minutes, 3-trifluoromethylphenyl acetic acid (3.0 g, 14.7 mmol), HOBT (3.177 g, 23.5 mmol), and EDC (3.10 g, 16.2 mmol) were added. The reaction mixture was stirred at room temperature for 18 h and was concentrated in vacuo. The residue was diluted with EtOAc and the organic solution was washed consecutively with 1N NaOH (2 times), water, and brine. The organic solution was dried (MgSO4), filtered and concentrated in vacuo. Medium pressure chromatography (20% EtOAc in hexanes to 50% EtOAc in hexanes) provided N-methoxy-N-methyl-2-(3-trifluoromethyl-phenyl)-acetamide.
Workup
- stirringThe reaction mixture was stirred at room temperature for 18 h
- concentrationwas concentrated in vacuo
- additionThe residue was diluted with EtOAc
- washthe organic solution was washed consecutively with 1N NaOH (2 times), water, and brine
- dry with materialThe organic solution was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-4ce752e9a7034a9b922b10a7fce8641d
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747054B2
Reaction notes
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