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

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

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.