Sodium hydride → HCID 22058664, compound

HRID 1072800Notes

Reaction equation

HRID 1072800 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[NH:5][C:6]=1[Br:7].[H-].[Na+].[CH3:11][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][O:15][CH2:16]Cl>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([CH3:8])[N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:12]([CH3:19])([CH3:18])[CH3:11])[C:6]=1[Br:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27733644,5-dibromo-2-methyl-1H-imidazole

Product 1

HCID 22058664HCID 22058664, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,5-Dibromo-2-methylimidazol (4.91 g) was dissolved in N,N-dimethyl-formamide (50 ml) and 60% sodium hydride (901 mg was gradually added under ice-cooling. The mixture was stirred for 1 hr at room temperature, and 2-(trimethylsilyl)ethoxymethyl chloride (3.75 g) was gradually added dropwise under ice-cooling and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and ethyl acetate was added to the residue. The residue was washed with a saturated aqueous sodium hydrogencarbonate solution, and then with brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the objective compound (7.6 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated under reduced pressure and ethyl acetate
  5. additionwas added to the residue
  6. washThe residue was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto remove the solvent The residue
  10. customwas purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-1e3965b439924abb9aa85a37bd615e8f
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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