Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 1814678Notes

Reaction equation

HRID 1814678 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[N:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl-].[NH4+].[N-:14]=[N+:15]=[N-:16].[Na+].Cl>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:14]=[N:15][NH:16][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120793-NitrobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 2851295-(3-nitrophenyl)tetrazoleYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

m-Nitrocyanobenzene (10 g, 67.5 mmol) was dissolved in DMF and ammonium chloride (7.2 g, 135 mmol) and sodium azide (8.8 g, 135 mmol) were added and the resulting mixture was stirred at 125° C. for 16 hours. After cooling to room temperature, the mixture was poured into water (1 L), acidified with 1 N hydrochloric acid and filtered immediately. The mother liquor was left for 1 hour and filtered and the solid was washed with water and dried by suction to afford 9.3 g (72%) 5-(3-nitrophenyl)-2H-tetrazole.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered immediately
  3. waitThe mother liquor was left for 1 hour
  4. filtrationfiltered
  5. washthe solid was washed with water
  6. customdried by suction

Sources & evidence

ORD record
ord-e3daeee1c2734c8cba4c6b94134f3684
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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