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

HRID 387475노트

반응식

HRID 387475 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-36550c2339804569ba8ac8848a68de12
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

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