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

HRID 36031

Reaktionsgleichung

Reaktionsgleichung von HRID 36031
[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 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 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-bebdd46407ed4d14828dd44daa521bd6
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412102

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