Water → N-[1-methyl-1-(3-chlorophenyl)ethyl]-N-(2-methyl-2-propenyl)-2-bromo-2-(2-fluorophenyl)acetamide
Reaction equation
N1C=CC=CC=1.[Br:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[C:9](Cl)=[O:10].[CH3:19][C:20]([NH:29][CH2:30][C:31]([CH3:33])=[CH2:32])([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH3:21].O>ClCCl>[CH3:21][C:20]([N:29]([CH2:30][C:31]([CH3:33])=[CH2:32])[C:9](=[O:10])[CH:8]([Br:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 30 ml of dichloromethane containing 2.8 g of pyridine, 4.0 g of 2-bromo-2-(2-fluorophenyl)acetyl chloride were added dropwise to 2.5 g of N-[1-methyl-1-(3-chlorophenyl)ethyl]-2-methyl-2-propenylamine at 10° to 15° C. After stirring at room temperature for 1 hour, the solution was poured into water, and extraction was then made with dichloromethane. The resultant extract was washed with a saturated aqueous sodium bicarbonate solution, and dried over anhydrous sodium sulfate. After concentration, column chromatography was done to obtain 2.0 g of the desired N-[1-methyl-1-(3-chlorophenyl)ethyl]-N-(2-methyl-2-propenyl)-2-bromo-2-(2-fluorophenyl)acetamide.
Workup
- extractionThe resultant extract
- washwas washed with a saturated aqueous sodium bicarbonate solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationAfter concentration, column chromatography
Sources & evidence
- ORD record
- ord-0f575fc5d47a4fbba2fe48695a78ad5b
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05352655
Reaction notes
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