Ethanol → Diethyl 1H-imidazole-4,5-dicarboxylate

HRID 366952

Reaktionsgleichung

[NH:1]1[C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:9]([OH:11])=[O:10])[N:3]=[CH:2]1.[CH2:12](N(CC)CC)[CH3:13].[CH2:19](O)[CH3:20]>ClCCl>[NH:1]1[C:5]([C:6]([O:8][CH2:12][CH3:13])=[O:7])=[C:4]([C:9]([O:11][CH2:19][CH3:20])=[O:10])[N:3]=[CH:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Imidazole-4,5-dicarboxylic acid (7.55 g, 50.0 mmol) is dissolved in absolute ethyl alcohol (120 mL). The solution was cooled in an ice bath to 0° C. and bubbled dry HCl gas for 1 h. Later, the reaction mixture was refluxed at 80° C. for 7 h during which time all the starting material was consumed. The solvent was removed and the residue that obtained was dissolved in dichloromethane (200 mL) and the organic layer was neutralized with triethylamine. The organic layer was washed with cold water (100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 5.50 g (52%) of white solid: mp 175-177° C.; 1H NMR (CDCl3) δ 1.40 (t, 3H), 4.41 (m, 2H), 7.84 (1H, C2H) and 11.55 (br s, 1H, NH).

Aufarbeitung

custombubbled dry HCl gas for 1 h
temperatureLater, the reaction mixture was refluxed at 80° C. for 7 h during which time all the starting material
customwas consumed
customThe solvent was removed
customthe residue that obtained
washThe organic layer was washed with cold water (100 mL) and brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-4c2bb86c51e7494198360f8e51c79249
Quelldatensatz: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06130326

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