Pyridine → 1-{2-(2-Fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

HRID 1747354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747354
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]([CH3:21])=[CH2:20])[C:11]1=[O:22].Cl.[NH2:25][OH:26].N1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:25][OH:26])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]([CH3:21])=[CH2:20])[C:11]1=[O:22]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 594974541-[2-(2-Fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

Produkt 1

HCID 723080691-{2-(2-Fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-oneAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 1-[2-(2-fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (1.3 g, 4.2 mmol) in ethanol (50 ml) was added hydroxylamine hydrochloride (0.84 g, 12.2 mmol) followed by pyridine (1.7 ml, 21.0 mmol) at ambient temperature. The resulting mixture was warmed to 80° C. for 6 h, cooled to ambient temperature and concentrated. The remaining residue was diluted with water, 1M HCl and ethyl acetate. The layers were separated and the aqueous phase was extracted once more with ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 50% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 1.0 g (73%) of the desired product as an oil which solidified on standing.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated
  3. additionThe remaining residue was diluted with water, 1M HCl and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted once more with ethyl acetate
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product which
  10. customwas purified via column chromatography (silica gel, 50% EtOAc/hexanes)
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3d71513c1a2c4c63b6c17463a7c809b7
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

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