2-Methoxybenzonitrile → 5-(2-Methoxyphenyl)-1H-tetrazole

HRID 129562

Reaktionsgleichung

Reaktionsgleichung von HRID 129562
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])#[N:2].C([Sn]([N:24]=[N+:25]=[N-:26])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1.C(OCC)C>[CH3:10][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[N:24]=[N:25][NH:26][N:2]=1

Komponenten

5

Edukt 2

HCID 810862-MethoxybenzonitrileHCID 4984872Tributyltin azide

Produkt 1

HCID 8589085-(2-Methoxyphenyl)-1H-tetrazoleAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 1-cyano-2-methoxybenzene (1.02 g, 7.7 mmol) and tributyltin azide (3.4 g, 10.0 mmol) in 3.0 mL of xylene was heated under reflux for 5 hours. The reaction mixture then was cooled and diluted with diethyl ether. Anhydrous hydrochloric acid was bubbled into the mixture and a white precipitate formed. The precipitate was collected by suction filtration and washed repeatedly with diethyl ether. Drying gave 5-(2-methoxyphenyl)-2H-tetrazole (1.33 g, 7.55 mmol).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe reaction mixture then was cooled
  4. customAnhydrous hydrochloric acid was bubbled into the mixture
  5. customa white precipitate formed
  6. filtrationThe precipitate was collected by suction filtration
  7. washwashed repeatedly with diethyl ether
  8. customDrying

Quellen und Nachweise

ORD-Eintrag
ord-24f3d94f5f7e4bb690354a44a4f20d20
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468867

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