3-Cyanopyridine → 5-(3-Pyridyl)tetrazole

HRID 391501Notes

Reaction equation

HRID 391501 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[N:8])[CH:2]=1.[N-:9]=[N+:10]=[N-:11].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[N:8]1[NH:9][N:10]=[N:11][C:7]=1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 793-CyanopyridineHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 1510915-(3-Pyridyl)tetrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

30 g (288 mmol) of 3-pyridinecarbonitrile, 28.1 g (432 mmol) of sodium azide (NaN3), and 23.1 g (432 mmol) of ammonium chloride were dissolved in 200 mL of DMF. The solution was reacted at 100° C. for 24 hours. Then, water was added to the acquired reactant. The resulting product was neutralized with hydrochloric acid and then filtered, obtaining 19.6 g (Y=46%) of a white solid.

Workup

  1. customThe solution was reacted at 100° C. for 24 hours
  2. filtrationfiltered
  3. customobtaining 19.6 g (Y=46%) of a white solid

Sources & evidence

ORD record
ord-41afb95e81ff48db9c82f539d8673436
Source dataset
uspto-grants-2013_02
Patent number
US08383932B2

Reaction notes

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