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

HRID 1048617

Reaktionsgleichung

Reaktionsgleichung von HRID 1048617
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl: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.O1CCCC1>[CH3:19][C:11]1[C:10]([Cl: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 27357701-Chloro-3-isocyanato-2-methylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

Produkt 1

HCID 1366461851-(2-Methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of aluminium chloride 4.71 g, sodium azide 6.89 g and tetrahydrofuran 100 mL was stirred with heating under reflux for one hour. After the reaction mixtures were cooled under ice-cooling, thereto were added a mixture of the above-mentioned 1-chloro-3-isocyanato-2-methylbenzene and tetrahydrofuran 10 mL and the resulting mixtures were stirred with heating under reflux for five hours. After cooling the mixtures, to a mixture of sodium nitrite 10.59 g and water 300 mL was added the reaction mixtures with stirring. The mixtures were acidified with concentrated hydrochloric acid and were extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and were then concentrated under reduced pressure to give 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazole-5-one.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for one hour
  3. customAfter the reaction mixtures
  4. temperaturewere cooled under ice-
  5. temperaturecooling
  6. additionwere added
  7. stirringthe resulting mixtures were stirred
  8. temperaturewith heating
  9. temperatureunder reflux for five hours
  10. temperatureAfter cooling the mixtures
  11. additionwas added
  12. customthe reaction mixtures
  13. stirringwith stirring
  14. extractionwere extracted with ethyl acetate
  15. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  16. concentrationwere then concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-32741cd822db46f59cef1825a0d38c2f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09380782B2

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