Phosphorus oxychloride → Ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate

HRID 1398759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398759
[Cl:1][C:2]1[C:10]2[NH:9][C:8](=O)[N:7]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]=2[C:5]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:8]1[N:7]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]2[C:5]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[N:9]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 68773903Ethyl 4-[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate

Produkt 1

HCID 68761768Ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoateAusbeute 34 %

Versuchsvorschrift

The solution of ethyl 4-[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]butanoate (6.8 g, 19.32 mmol) in phosphorus oxychloride (70 mL) was stirred at 100-110° C. for 2 days. After cooled to room temperature, the excess phosphorus oxychloride was removed by distillation and the residue was poured into water. The aqueous phase was extracted with ethyl acetate (100 mL×3) and the combined extracts were washed with saturated aqueous sodium bicarbonate (100 mL×2) and water (100 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column (petroleum ether/ethyl acetate, 50/1) to afford the title compound (2.4 g, 34%) as light yellow oil.

Aufarbeitung

  1. customthe excess phosphorus oxychloride was removed by distillation
  2. additionthe residue was poured into water
  3. extractionThe aqueous phase was extracted with ethyl acetate (100 mL×3)
  4. washthe combined extracts were washed with saturated aqueous sodium bicarbonate (100 mL×2) and water (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column (petroleum ether/ethyl acetate, 50/1)

Quellen und Nachweise

ORD-Eintrag
ord-2fd541fb4e9d45df98e7eb48ffbb619c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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