Methyl iodide → HCID 22130798, compound
Reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[NH:9][C:10]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)(=[O:3])[CH3:2].[C:28](=O)([O-])[O-].[K+].[K+].CI.CCCCCC>CN(C)C=O>[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[N:9]([CH3:28])[C:10]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 12 ml of dry dimethylformamide was dissolved 600 mg (1.4 mmol)of [2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1H-imidazol-4-yl]methyl acetate, followed by addition of anhydrous potassium carbonate (2.8 mmol). Then, 240 mg (1.7 mmol)of methyl iodide was added, and the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture, ice-water was added, extracted with diethyl ether, the organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:2)to obtain 288 mg of [2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1-methyl-1H-imidazol-4-yl]methyl acetate (47)as oil (yield 46%).
Workup
- extractionextracted with diethyl ether
- washthe organic layer was washed with water
- dry with materialdried over sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel chromatography (ethyl acetate
Sources & evidence
- ORD record
- ord-46024d429cc14fe8b1af601bdecc37f9
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05910506
Reaction notes
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