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

HRID 10703

Reaction equation

HRID 10703 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 962WaterSolvent2×

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-228157ee07eb44e19dc9905a42bbafbc
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Linked notes

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