Ethyl bromoacetate → ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)acetate

HRID 2059957

Reaktionsgleichung

Reaktionsgleichung von HRID 2059957
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[S:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 7070352-Mercaptobenzimidazole

Produkt 1

HCID 21564ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)acetateAusbeute 30.947,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 1H-benzo[d]imidazole-2(3H)-thione (20.0 g, 0.13 mol, 1.0 eq.) in anhydrous ethanol (500 mL) at room temperature, was added potassium carbonate (9.25 g, 0.07 mol, 0.5 eq.) and ethyl bromoacetate (26.7 g, 0.16 mmol, 1.2 eq.). The reaction was heated to reflux and stirred at that temperature for 6 hours. The solvent was removed in vacuo and water (200 mL) was added. The aqueous phase was extracted with dichloromethane (3×100 mL), and the combined organic extracts were washed with water (200 mL) and brine (200 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo to give a colorless oil which solidified on standing. Purification by flash chromatography (CHCl3→10% MeOH:90% CHCl3) gave 4a as a white solid (11.7 g, 37%).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo and water (200 mL)
  4. additionwas added
  5. extractionThe aqueous phase was extracted with dichloromethane (3×100 mL)
  6. washthe combined organic extracts were washed with water (200 mL) and brine (200 mL)
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a colorless oil which
  10. customPurification by flash chromatography (CHCl3→10% MeOH:90% CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-fd220d09049246eba6a85a82436efdbe
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278327B2

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