Phosphorus oxychloride → Isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate
Reaktionsgleichung
[Cl:1][C:2]1[C:10]2[NH:9][C:8](=O)[N:7]([CH2:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:6]=2[C:5]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:8]1[N:7]([CH2:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:6]2[C:5]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[N:9]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of isopropyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate (14.5 g, 42.8 mmol) and phosphorus oxychloride (60 mL) was stirred at 100° C. for 3 days. After cooling, phosphorus oxychloride was evaporated in vacuo. The residue was poured into ice-cold saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (×2). The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 5-15% ethyl acetate/n-hexane gradient mixture to give the title compound (14.1 g, 39.5 mmol, 92%) as an oil.
Aufarbeitung
- temperatureAfter cooling
- customphosphorus oxychloride was evaporated in vacuo
- additionThe residue was poured into ice-cold saturated aqueous sodium hydrogen carbonate
- extractionextracted with ethyl acetate (×2)
- washThe combined organic layer was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
- washeluting with a 5-15% ethyl acetate/n-hexane gradient mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-b2ddccd2305448399bee35df9bfcebcc
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08901141B2
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