Reaktionsgleichung
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7](OC)[CH:6]=1)=O.[CH:15]1([C:18]([NH2:20])=[NH:19])[CH2:17][CH2:16]1.[OH-].[Na+].[CH2:23]([OH:25])C>>[CH:15]1([C:18]2[NH:19][CH:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][C:10]=3[O:25][CH3:23])[N:20]=2)[CH2:17][CH2:16]1Komponenten
Versuchsvorschrift
Ex-105A: A solution of 2-bromo-1-(3,4-dimethoxy-phenyl)-ethanone (0.3 g, 1.16 mmol), cyclopropanecarboxamidine (0.14 g, 1.16 mmol) and sodium hydroxide (0.18 g, 4.5 mmol) in ethanol was refluxed overnight. The solvent was removed under reduced pressure, the residue taken up to water. The aqueous solution was then extracted with dichloromethane which was subsequently washed with brine, dried over sodium bicarbonate and concentrated. The crude product was purified by flash chromatography. Elution with ethyl acetate (50%, v/v, in hexane) then methanol (10%, v/v in dichloromethane) afforded 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole as white solid (0.1 5 g, 53%): 1HNMR (CDCl3) δ 9.50 (bs, 1H), 7.63 (s, 1H), 7.20 (s, 1H), 6.57–6.53 (m, 2H), 3.93 (s, 3H), 3.03 (s, 3H), 1.97–1.93 (m, 1H), 1.00–0.94 (m, 4H). MS m/z=245 ([M+H]+, 100%).
Aufarbeitung
- customThe solvent was removed under reduced pressure
- extractionThe aqueous solution was then extracted with dichloromethane which
- washwas subsequently washed with brine
- dry with materialdried over sodium bicarbonate
- concentrationconcentrated
- customThe crude product was purified by flash chromatography
- washElution with ethyl acetate (50%, v/v, in hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-bbb2cd7fd873464ea1dfd997d79efdb3
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07094801B2
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