N,N-Dimethylaniline → 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide
Reaction equation
N[C:2]1([N+:21]([O-])=O)[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]([CH3:14])=[N:4][CH:3]1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18].CN(C)C1C=CC=CC=1.[Br:33][CH2:34][C:35](Br)=[O:36]>ClCCl>[Br:33][CH2:34][C:35]([NH:21][C:2]1[C:3]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[N:4][C:5]([CH3:14])=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13])=[O:36]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-nitropyridine (42.29 g, 139.0 mmol) was dissolved in dichloromethane (600 mL), followed by the addition of N,N-dimethylaniline (20.46 g, 16.8 mmol). While stirring the mixture in an ice bath, a solution of bromoacetyl bromide (28.73 g, 142.3 mmol) in dichloromethane (100 mL) was added dropwise, and the reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was extracted with chloroform-water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from chloroform-hexane to obtain the title compound (50.25 g, 85%) as colorless needles.
Workup
- stirringthe reaction mixture was stirred at room temperature for 10 minutes
- extractionThe reaction mixture was extracted with chloroform-water
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was recrystallized from chloroform-hexane
Sources & evidence
- ORD record
- ord-0ccebef96cd3486f837a1f6bcd1197d2
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518936B2
Reaction notes
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