2,5-Hexanedione → 7-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one
Reaktionsgleichung
[NH2:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:18][C:17]1[N:1]([C:2]2[C:7]3[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)[C:14]([CH3:13])=[CH:15][CH:16]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a suspension of 257 mg (1.57 mmol) of 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one in 2 mL of acetic acid was added 0.18 mL (1.57 mmol) of 2,5-hexanedione, the mixture was stirred at 90° C. for 1 hour. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 25-50% ethylacetate/n-hexane gradient mixture to give 258 mg (68%) of the title compound.
Aufarbeitung
- temperatureAfter cooling
- extractionextracted with ethyl acetate (X2)
- washThe combined organic layer was washed with brine (X1)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
- washeluting with a 25-50% ethylacetate/n-hexane gradient mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-d60e54c0ab7f42a5b2bacd754876cdb7
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08163935B2
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