Sodium Azide → 2-Azido-5,6-dimethoxy-3-nitropyridine
Reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[N:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O>[N:15]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([O:11][CH3:12])=[C:4]([O:13][CH3:14])[N:3]=1)=[N+:16]=[N-:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 22.0 g of 2-bromo-5,6-dimethoxy-3-nitropyridine (example E4) in 50 ml DMSO were added 16.0 g sodium azide. The reaction mixture was stirred for 24 h at 50° C. Additional 3.20 g sodium azide were added and after stirring for additional 44 h the reaction was completed. The solvent was removed under vacuum and the resulting residue was extracted with dichloromethane (3×100 ml). The solvent was removed and the residue was purified by flash chromatography (petroleum ether/ethyl acetate) to yield the title compound.
Workup
- stirringafter stirring for additional 44 h the reaction
- customThe solvent was removed under vacuum
- extractionthe resulting residue was extracted with dichloromethane (3×100 ml)
- customThe solvent was removed
- customthe residue was purified by flash chromatography (petroleum ether/ethyl acetate)
Sources & evidence
- ORD record
- ord-45428190863e4b838b9a6b568d223db3
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273890B2
Reaction notes
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