Sodium Azide → 2-Azidopyridine

HRID 2267139Notes

Reaction equation

HRID 2267139 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[O-]S(C(F)(F)F)(=O)=O.F[N+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[N:1]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)

Product 1

HCID 109644722-AzidopyridineYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

Sodium azide (390 mg) was dissolved in 30 ml of methanol and cooled at −78° C., 6.0 ml of a methanolic solution of 740 mg of 1-fluoropyridinium triflate was dropped thereinto and the mixture was stirred for 4 hours. The solvent was evaporated in vacuo and the residue washed with 50 ml of diethyl ether to give 296 mg of the title compound in an ark oily crude product.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washthe residue washed with 50 ml of diethyl ether

Sources & evidence

ORD record
ord-53dca0e895a142b4bbc7fae9b0477e87
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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