Phosphorus oxychloride → 2-Chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole
Reaktionsgleichung
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]([F:20])([F:19])[F:18])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]([F:20])([F:19])[F:18])[C:10]=2[N:14]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
A mixture of 7-(1-ethylpropyl)-1-methyl-4-(trifluoro-methyl)-1,3-dihydro-2H-benzimidazol-2-one (310 mg, 1.08 mmol) and phosphoryl chloride (5 ml) was heated at 110° C. for 1 h and concentrated in vacuo. Toluene was added and concentrated again to remove excess reagent. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 20% ethyl acetate/n-hexane to give 300 mg (0.99 mmol, 91%) of the title compound as a colorless oil.
Aufarbeitung
- concentrationconcentrated in vacuo
- additionToluene was added
- concentrationconcentrated again
- customto remove excess reagent
- additionAqueous saturated sodium bicarbonate was added to the residue
- extractionextracted with ethyl acetate
- washThe extracts were washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel with a 20% ethyl acetate/n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-362cf988a8ee47c09f5151899e145138
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08163935B2
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