Imidazole → 1-[2-(2-Methoxyethoxy)ethyl]-1H-imidazole

HRID 2194957Notes

Reaction equation

HRID 2194957 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15].O>CN(C=O)C>[CH3:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 1235321-Bromo-3,6-dioxaheptane

Product 1

HCID 544832781-[2-(2-Methoxyethoxy)ethyl]-1H-imidazoleYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Imidazole 1 g (0.015 mol) was dissolved in dry DMF 50 mL under argon atmosphere. After a NaH mineral oil dispersion (60%) 0.68 g (0.017 mol) was added, the mixture was heated at 80° C. for 70 min. After cooling to room temperature, 1-Bromo-2-(2-methoxyethoxy)-ethane (1), 2.75 g (0.015 mol), was added, then stirred overnight. The reaction was poured into water, extracted by CHCl3, washed by water, dried over Na2SO4, then dried (Rotavap) until an oily residue remained. The crude product was purified with silica gel flash column chromatography with an eluant of CHCl3: CH3OH=20:1. 1.69 g (70% yield) of the product (2) was obtained as a colorless oil. As an alternative to column chromatography, product (2) is purified by vacuum distillation.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted by CHCl3
  3. washwashed by water
  4. dry with materialdried over Na2SO4
  5. customdried (Rotavap) until an oily residue
  6. customThe crude product was purified with silica gel flash column chromatography with an eluant of CHCl3

Sources & evidence

ORD record
ord-2dce1d926f1a439bb55c3273b29a2623
Source dataset
uspto-grants-2012_12
Patent number
US08334377B2

Reaction notes

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