Methyl iodide → 2-Methyl-5-phenyl-2H-tetrazole

HRID 29525Notes

Reaction equation

HRID 29525 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][NH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:14]I>>[CH3:14][N:9]1[N:10]=[N:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 874255-Phenyl-1H-tetrazole

Product 1

HCID 3297582-Methyl-5-phenyl-2H-tetrazoleYield 46%

Conditions

Temperature
0 °C

Procedure

5-phenyl-2-H-tetrazole (4 g, 27.36 mmol) was taken into NaOH (2.18 g, 54 mmol, dissolved in 10 ml of water), cooled to 0° C., methyl iodide (8.5 g, 60 mmol, dissolved in 40 ml acetone) was added and the reaction mixture was refluxed at 55° C. for 2 hours. The solvent was evaporated and the residue was dissolved in benzene. The benzene layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography using 60-120 mesh size silica gel (10% ethyl acetate in pet-ether as eluent) to obtain 2-methyl-5-phenyl-2H-tetrazole as white solid (2 g, 46%).

Workup

  1. temperaturethe reaction mixture was refluxed at 55° C. for 2 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in benzene
  4. washThe benzene layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d92022f21a7647798a0b7eafefeefa7c
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

Loading…