Cyanogen Bromide → 5-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide salt

HRID 387475

Reaktionsgleichung

Reaktionsgleichung von HRID 387475
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][NH2:15])=[O:13])=[CH:10][CH:9]=2)[CH:2]=1.[N:18]#[C:19][Br:20]>C1COCC1>[BrH:20].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]3[O:13][C:19]([NH2:18])=[N:15][N:14]=3)=[CH:16][CH:17]=2)[CH:2]=1

Komponenten

4

Edukt 2

HCID 10476Cyanogen BromideHCID 591354344-(Pyridin-3-yloxy)benzohydrazide

Produkt 1

HCID 686796585-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide saltAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(pyridine-3-yloxy)benzohydrazide (3.7 g, 16.14 mmol) was dissolved in 100 mL of anhydrous THF and 3.0 M solution of cyanogen bromide (5.38 mL, 16.14 mmol) was added via syringe. Within 5-10 min of stirring an orange precipitate started to form. The reaction mixture was brought to reflux and refluxed for 1 hr. Then it was cooled down to ambient temperature and filtered. The collected orange precipitate was washed with ca. 100 mL of THF, ca. 100 mL of EtOAc, anhydrous Et2O and dried in vacuo to give the title product as an orange solid (4.40 g). Yield 81.4%.

Aufarbeitung

  1. customto form
  2. temperatureto reflux
  3. temperaturerefluxed for 1 hr
  4. filtrationfiltered
  5. washThe collected orange precipitate was washed with ca. 100 mL of THF, ca. 100 mL of EtOAc, anhydrous Et2O
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36550c2339804569ba8ac8848a68de12
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372971B2

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