Sodium hydride → HCID 22058664, compound
Reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]([CH3:10])[NH:7][C:8]=1[Br:9].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>>[Br:3][C:4]1[N:5]=[C:6]([CH3:10])[N:7]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:8]=1[Br:9]Participants
Procedure
A 901 mg portion of 60% sodium hydride was added little by little to ice-cold N,N-dimethylformamide (50 ml) containing 4.91 g of 4,5-dibromo-2-methylimidazole. The reaction mixture was stirred at room temperature for 1 hour. 2-(Trimethysilyl)ethoxymethyl chloride (3.75 g) was added dropwise to the mixture on ice, and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, ethyl acetate was added to the resulting residue, and the mixture was washed subsequently with a saturated sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica-gel column chromatography (eluent, hexane:ethyl acetate=3:1) to obtain 7.6 g of colorless oily material of 4,5-dibromo-2-methyl-1-(2-(trimethylsilyl)ethoxymethyl)imidazole.
Workup
- stirringthe mixture was stirred at room temperature overnight
- customThe solvent was evaporated under reduced pressure, ethyl acetate
- additionwas added to the resulting residue
- washthe mixture was washed subsequently with a saturated sodium hydrogen carbonate aqueous solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe resulting residue was purified by silica-gel column chromatography (eluent, hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-8791a4efc0d6403684741ac0219ff584
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06242474B1
Reaction notes
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