Water → 1-Methoxymethyl-2-bromo-4,5-dichloroimidazole

HRID 979509Notes

Reaction equation

HRID 979509 reaction equation
[Br:1][C:2]1[NH:3][C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl.O>CN(C)C=O>[CH3:11][O:12][CH2:13][N:3]1[C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=[C:2]1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 994842-Bromo-4,5-dichloro-1H-imidazole

Product 1

HCID 137324141-Methoxymethyl-2-bromo-4,5-dichloroimidazoleYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.86 g of 2-bromo-4,5-dichloroimidazole in 5 ml of dimethylformamide was added 96 mg of sodium hydride at room temperature, and after standing for 30 minutes, 0.32 g of methoxymethyl chloride was added dropwise. The resulting mixture was stirred at room temperature for 1 hour, and after adding 40 ml of water, extracted with 30 ml of diethyl ether. Extraction with diethyl ether was repeated two more times, and the ether extract was dried over magnesium sulfate and concentrated to obtain an oily product. This product was purified by column chromatography on silica gel to obtain 0.40 g of 1-methoxymethyl-2-bromo-4,5-dichloroimidazole.

Workup

  1. extractionextracted with 30 ml of diethyl ether
  2. extractionExtraction with diethyl ether
  3. extractionthe ether extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain an oily product
  7. customThis product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-fa1f8a2617364c00bbc7abc9d511703f
Source dataset
uspto-grants-1987_05
Patent number
US04668693

Reaction notes

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