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

HRID 10703

反応式

HRID 10703 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒HCID 962Water溶媒2 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-228157ee07eb44e19dc9905a42bbafbc
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

関連ノート

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