Dimethylformamide → 5-(3-nitrophenyl)tetrazole

HRID 1588025Notes

Reaction equation

HRID 1588025 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1C#N)([O-:3])=[O:2].[N-:12]=[N+:13]=[N-:14].[Na+].[Cl-].[NH4+].[CH3:18][N:19](C)C=O>>[N+:1]([C:4]1[CH:5]=[C:8]([C:18]2[NH:19][N:14]=[N:13][N:12]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11922o-NitrobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 2851295-(3-nitrophenyl)tetrazole

Conditions

Temperature
110 °C

Procedure

Nitrobenzonitrile (5 g) was dissolved in 50 ml of dry N,N-dimethylformamide and mixed with 10.97 g of sodium azide and 9.03 g ammonium chloride. The resulting suspension was heated to 110° C. for 18 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in water (50 ml). The aqueous solution was washed with ethyl acetate and acidified with 1 N HCl solution. The aqueous phase was then extracted with ethyl acetate and the organic extracts were dried (sodium sulfate) and concentrated to give 8.5 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (50 ml)
  3. washThe aqueous solution was washed with ethyl acetate
  4. extractionThe aqueous phase was then extracted with ethyl acetate
  5. dry with materialthe organic extracts were dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4bd5dab0d3d14c05942cbc3d6c6ea563
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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