Sodium Azide → 3-bromo-5-nitrophenyl-1-methyl-1H-tetrazole

HRID 241677Notes

Reaction equation

HRID 241677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([NH:7][CH3:8])=O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:7]([CH3:8])[N:32]=[N:31][N:30]=2)[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 222526863-Bromo-N-methyl-5-nitrobenzamide

Product 1

HCID 222526903-bromo-5-nitrophenyl-1-methyl-1H-tetrazoleYield 44.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-N-methyl-5-nitro-benzamide (0.6 g) in DCM (15 ml) at −15° C. was added triflic anhydride (0.6 ml) and the reaction stirred for 30 min. Sodium azide (226 mg) was added and the reaction allowed to warm to room temperature and stirred further overnight. NaHCO3(aq) was added to neutralise the reaction and the mixture extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum and the residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc) to give the title compound (290 mg). R1=0.51 (3:2 cyclohexane:EtOAc).

Workup

  1. stirringstirred further overnight
  2. customthe reaction
  3. extractionthe mixture extracted into EtOAc
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated in vacuum
  7. customthe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

Sources & evidence

ORD record
ord-a0e59536df144b009924d9fc78337b73
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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