Sodium Azide → 1-(4-Bromophenyl)-1,2-dihydro-5H-tetrazol-5-one

HRID 718654Notes

Reaction equation

HRID 718654 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[Al+3].[Cl-].[Cl-].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:10])[NH:13][N:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 756094-Bromophenyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1362439061-(4-Bromophenyl)-1,2-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-isocyanatobenzene (5.0 g, 25 mmol) and sodium azide (5.0 g, 77 mmol) in THF (30 mL) was added a solution of AlCl3 (4.0 g, 30 mmol) in THF (18 mL) dropwise. The reaction mixture was heated to reflux overnight. The organic solvent was removed under reduced pressure, then water (50 mL) was added. The solids formed were collected by filtration to obtain compound 53a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C7H5BrN4O: 241.0 (M+H). Found 241.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe organic solvent was removed under reduced pressure
  4. additionwater (50 mL) was added
  5. customThe solids formed
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7df18866f5e34c23955575366b59a661
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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