Hydrochloric Acid → 1-[4-(2H-Tetrazol-5-yl)phenyl]ethan-1-one

HRID 10703

반응식

HRID 10703 반응식
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[N-:12]=[N+:13]=[N-:14].[Na+].Cl.CCOC(C)=O>O.[Br-].[Zn+2].[Br-]>[N:9]1[NH:12][N:13]=[N:14][C:8]=1[C:7]1[CH:10]=[CH:11][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 740444'-Cyanoacetophenone

생성물 1

HCID 214789301-[4-(2H-Tetrazol-5-yl)phenyl]ethan-1-one

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 962Water용매2회

실험 절차

Ex-78A: A suspension of 4-acetylbenznitrile (2.9 g, 20.0 mmol), sodium azide (1.43 g, 22.0 mmol) and zinc bromide (4.5 g, 20.0 mmol) in water (50 mL) was refluxed for one day. Additional water (40 mL), HCl (3M, 30 mL) and EtOAc (200 mL) were added subsequently. The mixture was stirred until no solid in the aqueous layer. The mixture was then portioned. The aqueous solution was further extracted with EtOAc (3×60 mL). The combined EtOAc was concentrated. The residue was treated with NaOH (0.25 M, 200 mL). After stirred for 50 min, insoluble material was filtered, washed with NaOH (1M). The filtrate was then acidified with HCl (conc.) to pH 3. The resulting white precipitate was filtered, washed with water and dried in vacuo to obtain 1-[4-(2H-tetrazol-5-yl)-phenyl]-ethanone as white solid. 1H NMR (DMSO-d6) δ 8.17–8.10 (m, 4H), 2.61 (s, 3H). MS m/z=188 (M+).

후처리

  1. temperaturewas refluxed for one day
  2. extractionThe aqueous solution was further extracted with EtOAc (3×60 mL)
  3. concentrationThe combined EtOAc was concentrated
  4. additionThe residue was treated with NaOH (0.25 M, 200 mL)
  5. stirringAfter stirred for 50 min
  6. filtrationinsoluble material was filtered
  7. washwashed with NaOH (1M)
  8. filtrationThe resulting white precipitate was filtered
  9. washwashed with water
  10. customdried in vacuo

출처 및 근거

ORD 기록
ord-228157ee07eb44e19dc9905a42bbafbc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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