Sodium Azide → HCID 178505536, compound

HRID 422422Notes

Reaction equation

HRID 422422 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[N+]([O-])=O)=[CH:8][CH:7]=1>CS(C)=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:1]=[N:2][NH:3][CH:13]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53816801-Fluoro-4-((1E)-2-nitroethenyl)benzene

Product 1

HCID 178505536HCID 178505536, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium azide (4.28 g, 65.8 mmol) was added to a solution (E)-1-fluoro-4-(2-nitro-vinyl)-benzene (1.00 g, 5.98 mmol) in DMSO (50 mL), the solution was stirred at room temperature for 14 hours and the reaction mixture was poured onto water. The aqueous phase was extracted with AcOEt. The organic phase was washed with saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated to yield 300 mg (1.84 mmol, 31%) of 4-(4-fluoro-phenyl)-1H-[1,2,3]triazole.

Workup

  1. additionthe reaction mixture was poured onto water
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with saturated solution of NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5dd571090d914aeabf9a745a6730e8f9
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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