Sodium Azide → HCID 17966438, compound

HRID 227588Notes

Reaction equation

HRID 227588 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]#[N:13])[C:7]=1[O:14][CH3:15]>CN(C)C=O.O>[N:1]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]#[N:13])[C:7]=1[O:14][CH3:15])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 17966439HCID 17966439, compound

Product 1

HCID 17966438HCID 17966438, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 1 g (0.0155 moles) of sodium azide in 25 ml of dimethylformamide at 0° C., there is added gently 3 g (0.0141 moles) of 4-bromo-2-cyano-3-methoxypyridine from Example b), dissolved in 40 ml of dimethylformamide. The mixture is stirred for 6 hours at ambient temperature. The reaction mixture is diluted in 200 ml of iced water and extracted with dichloromethane. The organic phase is washed twice with water, dried, concentrated and the residue chromatographed (ethyl acetate/heptane, 3:7). There is obtained 0.87 g (35% yield) of a white solid (MP=102° C.).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed twice with water
  3. customdried
  4. concentrationconcentrated
  5. customthe residue chromatographed (ethyl acetate/heptane, 3:7)

Sources & evidence

ORD record
ord-75eb3713237b4230bb316efd166e9b1d
Source dataset
uspto-grants-2009_07
Patent number
US07560565B2

Reaction notes

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