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

HRID 247853

Reaction equation

HRID 247853 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:6](OCC)([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:8]([O:7][CH:6]([O:10][CH2:11][CH3:12])[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH3:9]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 31214Ethyl orthoformate

Product 1

HCID 38495351-(diethoxymethyl)-1H-imidazoleYield 72.4%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
130 °C

Procedure

Imidazole (6.81 g, 0.10 mol, 1.0 eq), triethyl orthoformate (66.5 mL, 0.40 mol, 4.0 eq) and para-toluenesulfonic acid (0.5 g) were combined and heated at 130° C. Ethanol was slowly distilled off. After the distillation of the ethanol ceased, the reaction was distilled using a floor pump (0.1 mm). Excess triethyl orthoformate distilled at 50° C. and then the product was distilled at 78°-84° C. to give the title compound (12.316 g, 72%). B. 2-Butyl-1H-imidazole

Workup

  1. distillationEthanol was slowly distilled off
  2. distillationAfter the distillation of the ethanol
  3. distillationthe reaction was distilled
  4. distillationExcess triethyl orthoformate distilled at 50° C.
  5. distillationthe product was distilled at 78°-84° C.

Sources & evidence

ORD record
ord-06b1da150e4241318a794b79309b0d3b
Source dataset
uspto-grants-1993_05
Patent number
US05208235

Linked notes

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