Acetamide → 2-((2-Bromopyridin-3-yl)oxy)acetamide

HRID 1517589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517589
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[C:11]([NH2:14])(=[O:13])[CH3:12]>O1CCCC1>[Br:1][C:2]1[C:7]([O:8][CH2:12][C:11]([NH2:14])=[O:13])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 178AcetamideHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Produkt 1

HCID 478080992-((2-Bromopyridin-3-yl)oxy)acetamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-3-pyridinol (1.5 g, 8.49 mmol) in tetrahydrofuran (15 mL) at 0° C. is added 60% sodium hydride in mineral oil (509.44 mg, 12.74 mmol) and the mixture is stirred at that temperature for 30 min. Then acetamide, 2-chloro-(16.98 mmol) is added and the mixture is stirred at room temperature over the weekend. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is separated dried on magnesium sulfate and the solvent evaporated in vacuo to give the title compound in a 75% yield. The compound is used without any further purification. MS (m/z): 231 (M+1), 233 (M+3).

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature over the weekend
  2. customThe mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is separated
  5. customdried on magnesium sulfate
  6. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c186365d799849169d3bd529860bdbeb
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232289B2

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