Imidazole → 1-(Ethoxymethyl)-1H-imidazole

HRID 1865735Notes

Reaction equation

HRID 1865735 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:8]([O:10][CH2:11]Cl)[CH3:9]>CS(C)=O>[CH2:8]([O:10][CH2:11][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride

Product 1

HCID 130194491-(Ethoxymethyl)-1H-imidazoleYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of imidazole (10.0 g, 146.9 mmole) in 100 ml dimethyl sulfoxide at room temperature under nitrogen is added sodium hydride (6.46 g, 161.6 mmole). The solution is stirred at 80° C. for 2 hours. Chloromethyl ethyl ether (16.35 ml, 176.3 mmole) is added dropwise. The reaction mixture is stirred for another 2 hour at 80° C., cooled to room temperature, poured into 5% aqueous solution and extracted with dichloromethane (4×200 ml). The combined organic extracts are dried over sodium sulfate, filtered, concentrated in vacuo. The residue is fresh chromatographed in hexane/ethyl acetate from 5:1 to 2:1 to give 1-ethoxymethyl-1H-imidazole as a brown oil 1.68 g (90%) MS (ES+): (M+H)=127.0

Workup

  1. stirringThe reaction mixture is stirred for another 2 hour at 80° C.
  2. temperaturecooled to room temperature
  3. extractionextracted with dichloromethane (4×200 ml)
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is fresh chromatographed in hexane/ethyl acetate from 5:1 to 2:1

Sources & evidence

ORD record
ord-b7e61afef4d745af963e11e6bb3f8018
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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