Methyl iodide → N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide
Reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[O:6].[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:17][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH3:20])[C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[O:6]Participants
Procedure
To a suspension of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide (5) (22.07 g, 95 mmol) in anhydrous dimethylformamide (114 mL) under nitrogen in an ice bath is added sodium hydride (Aldrich, 60% in mineral oil) (4.75 g, 119 mmol) and, within 15 minutes, the gas evolution has ceased. To the above reaction mixture is added a solution of methyl iodide (Aldrich) (14.2 g, 99.8 mmol). The reaction mixture is stirred overnight and allowed to warm to room temperature. The reaction is triturated with hexane (3×150 mL) which is discarded. The reaction mixture is poured into ice water, extracted with dichloromethane (3×200 mL) which is dried with anhydrous sodium sulfate. The dry dichloromethane is concentrated to yield a solid, which is triturated with a solution of ethyl acetate and hexane (1:1, 200 m l). Product (6) is obtained as an orange solid (16.9 g, 68.6 mmol, 72%).
Workup
- customThe reaction is triturated with hexane (3×150 mL) which
- additionThe reaction mixture is poured into ice water
- extractionextracted with dichloromethane (3×200 mL) which
- dry with materialis dried with anhydrous sodium sulfate
- concentrationThe dry dichloromethane is concentrated
- customto yield a solid, which
- customis triturated with a solution of ethyl acetate and hexane (1:1, 200 m l)
Sources & evidence
- ORD record
- ord-0e509f7713c34506a70ee634ddab9c06
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06399621B1
Reaction notes
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