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

HRID 1772616Notes

Reaction equation

HRID 1772616 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+].[Cl-].[Cl-].[Cl-].[Al+3]>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-oneYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-isocyanatobenzene (5.00 g, 25.4 mmol) in THF (30 mL) was added sodium azide (5.00 g, 76.9 mmol) followed by the addition of a solution of aluminum trichloride (4.00 g, 30.3 mmol) in THF (18 mL) slowly. The reaction mixture was heated to reflux overnight. After cooling to rt, the reaction was quenched with H2O (50 mL). The organic solvent was removed under reduced pressure. The solids were collected by filtration to obtain compound 14a as a white solid (4.50 g, 71% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C2H5BrN4O: 241.0 (M+H). Found 241.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customthe reaction was quenched with H2O (50 mL)
  4. customThe organic solvent was removed under reduced pressure
  5. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-43de58c07c3444d089f086aa8cbe8ac2
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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