Sodium Azide → 2-Azido-1-oxo-1lambda~5~-quinoxaline
Reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N+:3]=1[O-:12].[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O.O>[N:13]([C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N+:3]=1[O-:12])=[N+:14]=[N-:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
In this example 0.500 grams (0.0028 mol) of 2-chloroquinoxaline 1-oxide and 0.500 grams (0.0080 mol) of sodium azide were added to and dissolved in 35 ml of acetone and 35 ml of water. The solution was stirred at 25° C for 60 hours. The acetone was evaporated in vacuo and the resulting aqueous solution was extracted with methylene chloride. The organic phase was introduced onto a basic alumina column. Elution with chloroform gave 2 azidoquinoxaline-oxide in a yield of 0.080 grams or 16% of theory which was immediately decomposed in boiling benzene for 1 hour. Evaporation of the solvent gave 2-cyanobenzimidazole N-oxide which is tautomeric with N-hydroxy-2-cyanobenzimidazole in a yield of 0.020 grams or 30% of theory having a melting point of 236° C to 238° C with decomposition.
Workup
- customThe acetone was evaporated in vacuo
- extractionthe resulting aqueous solution was extracted with methylene chloride
- additionThe organic phase was introduced onto a basic alumina column
- washElution with chloroform
Sources & evidence
- ORD record
- ord-ed09864c0c6546769cc5d6a61c1a4a83
- Source dataset
- uspto-grants-1977_02
- Patent number
- US04006160
Reaction notes
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