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

HRID 1994048Notes

Reaction equation

HRID 1994048 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 Et2O 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 Et2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-353b2cdca5f945c791a8fc10fdd6129d
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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