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

HRID 661429Notes

Reaction equation

HRID 661429 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 686796585-[4-(Pyridin-3-yloxy)phenyl]-1,3,4-oxadiazol-2-amine hydrobromide saltYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 Et20 and dried in vacuo to give the title product as an orange solid (4.40 g). Yield 81.4%.

Workup

  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 Et20
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a8caea0ed74f46ae884ec03679daad0f
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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