Sodium Azide → 6-Azidomethylnicotinonitrile

HRID 1355598Notes

Reaction equation

HRID 1355598 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.C(OCC)C.O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)=[N+:12]=[N-:13]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 219277766-(Bromomethyl)pyridine-3-carbonitrile

Product 1

HCID 185067406-AzidomethylnicotinonitrileYield 101.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-Bromomethylnicotinonirile (11-2) (8.0 g, 40.6 mmol) in DMF (100 ml) was added sodium azide (3.17 g, 48.8 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with 400 ml diethylether and 100 ml water and the layers were separated. The aqueous layer was re-extracted with diethylether (2×100 ml). The combined ether extracts were washed with brine (2×100 ml) and then dried over MgSO4 and filtered to yield 6.53 g product as a white solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was re-extracted with diethylether (2×100 ml)
  3. washThe combined ether extracts were washed with brine (2×100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-911313485245492b9e52aeb8cff44ca9
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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