Sodium Azide → HCID 178514477, compound

HRID 1461317Notes

Reaction equation

HRID 1461317 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([OH:14])=[N:5]2.N([O-])=O.[Na+].[N-:19]=[N+:20]=[N-].[Na+]>F[B-](F)(F)F.[H+].O>[N:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([OH:14])=[N:5]2)=[N+:19]=[N-:20]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 178507221HCID 178507221, compound

Product 1

HCID 178514477HCID 178514477, compoundYield 757.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 28118Tetrafluoroboric acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2 g (9,6 mmol) 6-amino-7-chloro-2,3-dihydroxyquinoxaline in 40 ml 50% fluoroboric acid was added 100 ml water, filtered and then ice-cooled. A solution of 0,68 g (9,9 mmol) sodium nitrite in 20 ml water was added, and after stirring at 0° C. for 15 min. 0,68 g (1,0 mmol) sodium azide dissolved in 20 ml water was added. Stirring was continued at 25° C. for 2 h. The precipitate was filtered off and washed with water to give 1,8 g (80%) 6-azido-7-chloro-2,3-dihydroxyquinoxaline. IR (KBr): 2100 cm-1 (N3). NMR (DMSO-d6): 11.7 (2H, broad s), 7.03 (1H,s), 6.93 (1H,s).

Workup

  1. filtrationfiltered
  2. temperatureice-cooled
  3. additionwas added
  4. stirringStirring
  5. waitwas continued at 25° C. for 2 h
  6. filtrationThe precipitate was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-29ca48aac3644e12bc71b058c2f09f82
Source dataset
uspto-grants-1991_12
Patent number
US05075306

Reaction notes

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