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

HRID 129562

Reaction equation

HRID 129562 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 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).

Workup

  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

Sources & evidence

ORD record
ord-24f3d94f5f7e4bb690354a44a4f20d20
Source dataset
uspto-grants-1995_11
Patent number
US05468867

Linked notes

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