Ammonium Chloride → methyl 2-(2H-tetrazol-5-yl)benzoate

HRID 1658459Notes

Reaction equation

HRID 1658459 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[N-:13]=[N+:14]=[N-:15].[Na+].[Cl-].[NH4+]>>[N:2]1[NH:13][N:14]=[N:15][C:1]=1[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 582554Methyl 2-cyanobenzoate

Product 1

HCID 21527413methyl 2-(2H-tetrazol-5-yl)benzoate

Procedure

Methyl 2-cyanobenzoate (54 g, 0.33 mole) in D.M.F. (165 ml) was treated with sodium azide (23.4 g, 0.36 mole) and ammonium chloride (19.3 g, 0.36 mole). After the reaction mixture had been stirred on the steam bath for 20 hrs., the D.M.F. was removed under reduced pressure and the residue dissolved in water (200 ml). The solution was filtered, cooled in ice and acidified to give a white precipitate which was filtered, washed with water and dried. This gave methyl 2-(5-2H-tetrazolyl)benzoate, M.P. 132°-5°, 19 g (28%). (Found: C, 53.79, 52.59, 52.33; H, 4.25, 4.17, 4.07; N, 26.79, 26.84, 27.25. C9H8N4O2 requires C, 52.94; H, 3.95; N, 27.44.)

Workup

  1. customwas removed under reduced pressure
  2. dissolutionthe residue dissolved in water (200 ml)
  3. filtrationThe solution was filtered
  4. temperaturecooled in ice
  5. customto give a white precipitate which
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-0944ccf091a141868a777fe897507993
Source dataset
uspto-grants-1976_06
Patent number
US03964896

Reaction notes

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