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

HRID 1757493

Reaktionsgleichung

Reaktionsgleichung von HRID 1757493
[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 5hours. 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 5hours
  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-4592e26b89c444cbade63ed2b263f723
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446121

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