Chloromethyl Methyl Ether → 1-(Methoxymethyl)-4,5-dimethylimidazole

HRID 261950Notes

Reaction equation

HRID 261950 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH3:9].Cl[CH2:11][O:12][CH3:13]>C(#N)C>[CH3:11][O:12][CH2:13][N:5]1[C:4]([CH3:3])=[C:8]([CH3:9])[N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 753064,5-Dimethyl-1H-imidazole

Product 1

HCID 213213081-(Methoxymethyl)-4,5-dimethylimidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At a temperature of 60° C., 500 mg. of picrinic acid and 15.6 g. (0.39 mol) of sodium hydroxide were added to a solution of 31 g. (0.32 mol) of 4,5-dimethylimidazole (H, Bredereck and G. Theilig, Chem. Ber. 86, 88 (1953)) in 150 ml. of acetonitrile. Then 29 g. (0.36 mol) of chloromethoxymethane were added drop-wise, which made the temperature rise to 80° C. The reaction mixture was refluxed for 6 hours and filtered. The filtrate was concentrated by distilling off the solvent and the residue was distilled. 1-(Methoxymethyl)-4,5-dimethylimidazole was obtained. Boiling point 80°-100° C./1.0 mm. Hg. Melting point of the hydrogen oxalate 102°-103° C.

Workup

  1. customAt a temperature of 60° C., 500 mg
  2. customto 80° C
  3. temperatureThe reaction mixture was refluxed for 6 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. distillationby distilling off the solvent
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-e2f1013cd2574a86ae28a0278895aeee
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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