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

HRID 247855Notes

Reaction equation

HRID 247855 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].C([O-])([O-])[O-].C(=O)(O)[O-].[Na+]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[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

7

Reactant 4

HCID 795ImidazoleHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 21585117Orthoformate

Product 1

HCID 38495351-(diethoxymethyl)-1H-imidazoleYield 68%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

A mixture of imidazole (15 g, 0.220 mol, 1 eq), triethyl orthoformate (130 g, 146.6 mL, 0.880 mol, 4.0 eq) and p-toluenesulfonic acid (1.17 g, 0.00616 mol, 0.028 eq) was heated at 145°-175° C. until no more ethanol was distillable from the reaction mixture. The excess orthoformate was removed in vacuo, solid sodium bicarbonate (1.17 g, 0.011 mol) was added and the residue was vacuum distilled to give the title compound (23.6 g, 68 %). b.p. 89°-91° C./0.3 mm Hg.

Workup

  1. additionwas added
  2. distillationdistilled

Sources & evidence

ORD record
ord-d09d35e436fe46b2b7aae01e3ecbe84b
Source dataset
uspto-grants-1993_05
Patent number
US05208235

Reaction notes

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