Ethanol → Ethyl 2-bromo-1-(2-butynyl)-5-cyano-1H-imidazole-4-carboxylate
Reaktionsgleichung
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[N:8]([CH2:16][C:17]#[C:18][CH3:19])[C:9]([C:14]#[N:15])=[C:10]([C:12]#N)[N:11]=1.[CH2:20]([OH:22])[CH3:21]>>[Br:6][C:7]1[N:8]([CH2:16][C:17]#[C:18][CH3:19])[C:9]([C:14]#[N:15])=[C:10]([C:12]([O:22][CH2:20][CH3:21])=[O:2])[N:11]=1Komponenten
Versuchsvorschrift
25 ml of concentrated sulfuric acid was added to a 500 ml ethanol solution of 48.0 g of 2-bromo-1-(2-butynyl)-1H-imidazole-4,5-dicarbonitrile, and the mixture was heated under reflux for 110 hours. The reaction solution was cooled to room temperature, and then concentrated under reduced pressure. The residue was dissolved in a mixture consisting of 500 ml of ethyl acetate and 500 ml of water, and the pH of the solution was adjusted to 8 using potassium hydroxide. The aqueous layer was extracted with 500 ml of ethyl acetate, and the organic layers were combined together. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 21.7 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (1:3).
Aufarbeitung
- temperaturethe mixture was heated
- temperatureunder reflux for 110 hours
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in a mixture
- extractionThe aqueous layer was extracted with 500 ml of ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-69b02d5c254340938f151da0f2a7225f
- Quelldatensatz
- uspto-grants-2010_08
- Patentnummer
- US07772226B2
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