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

HRID 247820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247820
[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]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 31214Ethyl orthoformateHCID 516892Sodium Bicarbonate

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

Quellen und Nachweise

ORD-Eintrag
ord-6a6261fd93044ce19dd1236baf1910f1
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208234

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