Sodium Azide → HCID 89619254, compound

HRID 1502057Notes

Reaction equation

HRID 1502057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([N+:12]([O-])=O)[C:4]=1[CH3:15].[N-:16]=[N+:17]=[N-].[Na+]>CS(C)=O>[N:12]([C:5]1[C:4]([CH3:15])=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10])=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 89619360HCID 89619360, compound

Product 1

HCID 89619254HCID 89619254, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-methoxy-2-methyl-3,4-dinitrobenzene (3.4 g, 16 mmol) in 60 mL of DMSO was added NaN3 (2.1 g, 32 mmol) at one portion and the reaction was stirred for 72 hours at room temperature. Then the reaction was poured into 500 mL of ice water, and then was extracted with DCM (100 mL×3). The combined organic layers were washed with water, dried and concentrated to about 100 mL of solvent. Then 100 mL of toluene was added and the residual DCM was removed under reduced pressure, the toluene solution of 2-azido-4-methoxy-3-methyl-1-nitrobenzene was used directly the next step.

Workup

  1. extractionwas extracted with DCM (100 mL×3)
  2. washThe combined organic layers were washed with water
  3. customdried
  4. concentrationconcentrated to about 100 mL of solvent
  5. additionThen 100 mL of toluene was added
  6. customthe residual DCM was removed under reduced pressure

Sources & evidence

ORD record
ord-01e1f893d3cd4a9a9ed62c690b08c64c
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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