N-(4-Methoxyphenyl)Acetamide → N-(4-methoxyphenyl)-N-(2-methylallyl)acetamide
Reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl[CH2:22][C:23]([CH3:25])=[CH2:24]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]([CH2:24][C:23]([CH3:25])=[CH2:22])[C:2](=[O:3])[CH3:1])=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 75 °C
Procedure
To a solution of p-acetanisidide (1.00 g, 6.05 mmol), potassium carbonate (0.92 g, 6.7 mmol), sodium hydroxide (0.27 g, 6.8 mmol) and tetra-n-butylammoniumbromide (0.39 g, 1.2 mmol) in 10 mL of toluene was added 3-chloro-2-methyl-1-propene (0.71 mL, 7.3 mmol) at room temperature. After the reaction mixture was stirred at 75° C. for 4 h, the reaction mixture was cooled to room temperature, and was diluted with ethyl acetate. The solution was washed with water, 3 M HCl, saturated NaHCO3 aqueous solution and brine, successively, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound (1.26 g, 95%).
Workup
- temperaturethe reaction mixture was cooled to room temperature
- washThe solution was washed with water, 3 M HCl, saturated NaHCO3 aqueous solution and brine
- dry with materialsuccessively, and dried over MgSO4
- filtrationAfter filtration
- concentrationthe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)
Sources & evidence
- ORD record
- ord-6b9516719e1e4b1eb3860237e2e67bec
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686024B2
Reaction notes
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