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

HRID 1795261Notes

Reaction equation

HRID 1795261 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) δ 9.44 (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-1fdba3ae423d4c1980ae4fa93598f0e0
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

Loading…