N-bromobutanimide → 2-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

HRID 1921820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921820
[S:1]1[C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:17])C(=O)C1>C(#N)C>[Br:17][C:2]1[S:1][C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 205428054H,5H,6H-thieno[2,3-c]pyrrol-6-one

Produkt 1

HCID 590231412-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4,5-Dihydro-thieno[2,3-c]pyrrol-6-one (0.365 g, 2.63 mmol) is dissolved in acetonitrile (10 mL), and NBS (0.47 g, 2.63 mmol) is slowly added at −10° C. The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue taken-up in EtOAc and washed with 1M NaOH. The organic phase is dried over MgSO4, filtered and concentrated in vacuo. The crude is purified by silica gel column chromatography eluting with a 50:50 mixture and then 50:70 petroleum ether-EtOAc. The title compound is isolated (91.1 mg, 16%). HPLC (254 nm): Rt 2.55 min (70.3%), m/z 218/220 (M+H)+.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. washthe residue taken-up in EtOAc and washed with 1M NaOH
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude is purified by silica gel column chromatography
  7. washeluting with a 50:50 mixture

Quellen und Nachweise

ORD-Eintrag
ord-25f33f57b63b40c392bd8ad9b5d2e7da
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173656B2

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