Hydrochloric Acid → Ethyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

HRID 1628389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628389
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:10]2[C:11]([CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][CH:13]=[CH:14][C:9]=2[N:8](C(OC(C)(C)C)=O)[C:7]1=[O:27])[CH3:2].Cl>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:16]([CH:15]([C:11]1[C:10]2[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:28])[C:7](=[O:27])[NH:8][C:9]=2[CH:14]=[CH:13][CH:12]=1)[CH2:18][CH3:19])[CH3:17]

Komponenten

5

Edukt 2

HCID 313Hydrochloric Acid2×HCID 68548443tert-Butyl 3-(2-ethoxy-2-oxoethyl)-4-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate

Produkt 1

HCID 86632858Ethyl [7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittel4×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 3-(2-ethoxy-2-oxoethyl)-4-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate (6.16 g, 15.8 mmol) in ethyl acetate (15 mL) was added a 4N solution of hydrogen chloride in ethyl acetate (15 mL) at 0° C., and the mixture was stirred at the same temperature for 2 hr. An additional 4N solution of hydrogen chloride in ethyl acetate (15 mL) was added to the mixture at 0° C., followed by stirring at the same temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting solid was washed with n-hexane to give the title compound (4.28 g, 14.7 mmol, 93%) as a colorless crystal.

Aufarbeitung

  1. stirringby stirring at the same temperature for 1 hr
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe resulting solid was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-25a523de718241ab9ff33dee61f8ddf6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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