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

HRID 2059641Notes

Reaction equation

HRID 2059641 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). Rf=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-e3a0e16ac7f0462b81d2a8375ae3865c
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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