Ammonium Chloride → 2-(1H-Tetrazol-1-YL)benzamide

HRID 397513Notes

Reaction equation

HRID 397513 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8](O)=[O:9])[CH:5]=[N:4][N:3]=[N:2]1.[Cl-].[NH4+].Cl.C[N:19](C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:19])=[O:9])[CH:5]=[N:4][N:3]=[N:2]1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 7536082-(1H-1,2,3,4-tetrazol-1-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 8559562-(1H-Tetrazol-1-YL)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-Tetrazol-1-yl-benzoic acid (1.0 g, 5.2 mmol), ammonium chloride (0.56 g, 10.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.0 g, 10.4 mmol), 1-hydroxy-7-azabenzotriazole (1.4 g, 10.4 mmol) and diisopropylethylamine (3.6 ml, 20.8 mmol) in N,N-dimethylformamide (15 ml) was stirred at room temperature overnight. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 2-Tetrazol-1-yl-benzamide; 1H NMR (CD3OD, 400 MHz) δ9.44 (s, 1H), 7.72 (m, 4H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-2c07656da277437f88a9d3ddd0e19e86
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

Loading…