Hydrochloric Acid → 1-(2-Methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one

HRID 1048619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048619
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]=[C:17]=[O:18])[C:11]=1[CH3:19].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH3:19][C:11]1[C:10]([Br:9])=[CH:15][CH:14]=[CH:13][C:12]=1[N:16]1[C:17](=[O:18])[NH:7][N:6]=[N:5]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium NitriteHCID 655423311-Bromo-3-isocyanato-2-methyl-benzene

Produkt 1

HCID 1366461861-(2-Methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-oneAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under ice-cooling, to N,N-dimethylformamide 220 mL was added anhydrous aluminum chloride 19.7 g and the resulting mixtures were stirred for fifteen minutes. Thereto was added sodium azide 9.6 g and the resulting mixtures were stirred for fifteen minutes and thereto was then added 1-bromo-3-isocyanato-2-methylbenzene 30.3 g and the resulting mixtures were heated at 80° C. for five hours. After cooling the mixtures, to a mixture of sodium nitrite 33 g, water 2 L and ice 500 g was added the reaction solutions with stirring. The mixtures were acidified with 10% hydrochloric acid and were extracted with ethyl acetate. The organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazole-5-one 31.4 g.

Aufarbeitung

  1. stirringthe resulting mixtures were stirred for fifteen minutes
  2. temperatureAfter cooling the mixtures
  3. additionwas added the reaction solutions
  4. stirringwith stirring
  5. extractionwere extracted with ethyl acetate
  6. washThe organic layers were washed with water and saturated saline
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. concentrationwere then concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d442d0aec58746beb02aa3cf9068cbe7
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09380782B2

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