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

HRID 36031

Reaction equation

HRID 36031 reaction equation
[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

Participants

5

Reactant 2

HCID 810862-MethoxybenzonitrileHCID 4984872Tributyltin azide

Product 1

HCID 8589085-(2-Methoxyphenyl)-1H-tetrazoleYield 98.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bebdd46407ed4d14828dd44daa521bd6
Source dataset
uspto-grants-1995_05
Patent number
US05412102

Linked notes

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