2-Propanone, 1-(acetyloxy)-3-chloro- → (6-Iodoimidazo[1,2-b]pyridazin-2-yl)methanol

HRID 1663669

Reaktionsgleichung

Reaktionsgleichung von HRID 1663669
[NH2:1][C:2]1[N:3]=[N:4][C:5]([I:8])=[CH:6][CH:7]=1.C([O:12][CH2:13][C:14](=O)[CH2:15]Cl)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:15]=[C:14]([CH2:13][OH:12])[N:1]=2)[N:4]=1

Komponenten

5

Edukt 3

HCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 516892Sodium BicarbonateHCID 108678346-Iodopyridazin-3-amine

Produkt 1

HCID 57441048(6-Iodoimidazo[1,2-b]pyridazin-2-yl)methanolAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-6-iodopyridazine (2.0 g, 9.0 mmol) in ethanol (40 mL) was added 3-chloro-2-oxopropyl acetate (2.73 g, 18.1 mmol), and the mixture was heated under reflux for 24 hr. After cooling the mixture to room temperature, saturated aqueous sodium hydrogencarbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate/hexane to give the title compound (498 mg, 20%) as a white powder.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationthe residue was collected by filtration
  9. washwashed with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-48c59711bfb14292b8b641f748ac35ac
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08034812B2

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