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

HRID 247820

Reaction equation

HRID 247820 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-].[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

6

Reactant 3

HCID 795ImidazoleHCID 31214Ethyl orthoformateHCID 516892Sodium Bicarbonate

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, 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. customThe excess orthoformate was removed in vacuo
  2. distillationdistilled

Sources & evidence

ORD record
ord-6a6261fd93044ce19dd1236baf1910f1
Source dataset
uspto-grants-1993_05
Patent number
US05208234

Linked notes

Loading…