Methyl iodide → 1-Methyl-2-nitroimidazole
Reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[C:9](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-nitro-1H-imidazole (500 mg, 4.4 mmol) in DMF (50 mL) is added cesium carbonate (1.7 g, 5.3 mmol) and the mixture is heated to 50° C. for 30 minutes. The resulting suspension is cooled to room temperature and MeI (0.33 mL, 5.3 mmol) is added. The reaction is heated to 50° C. for 2 hours is then cooled to room temperature and filtered through a bed of Celite. The filtrate is poured over ice water and extracted ethyl acetate. The organic layer is washed with water, brine, dried (Na2SO4) and concentrated to afford the title compound (485 mg, 86%) as a yellow solid.
Workup
- temperatureThe resulting suspension is cooled to room temperature
- temperatureThe reaction is heated to 50° C. for 2 hours
- temperatureis then cooled to room temperature
- filtrationfiltered through a bed of Celite
- additionThe filtrate is poured over ice water
- extractionextracted ethyl acetate
- washThe organic layer is washed with water, brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-84215856237d4966afe000441842fd5e
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150577B2
Reaction notes
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