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

HRID 247855

Reaktionsgleichung

Reaktionsgleichung von HRID 247855
[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]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 21585117Orthoformate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added
  2. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-d09d35e436fe46b2b7aae01e3ecbe84b
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208235

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