4-Formylbenzoic acid → 4-formyl-N-(2H-tetrazol-5-yl)benzamide

HRID 1814655Notes

Reaction equation

HRID 1814655 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)(O)=[O:2].O.[NH2:13][C:14]1[NH:18][N:17]=[N:16][N:15]=1>CN(C=O)C>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([NH:13][C:14]2[N:15]=[N:16][NH:17][N:18]=2)=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

4

Reactant 2

HCID 120884-Formylbenzoic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 225017874-formyl-N-(2H-tetrazol-5-yl)benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-carboxybenzaldehyde (40.2 g, 0.27 mol) in DMF (400 mL) was added N-ethyl-N′-3-dimethylaminopropylcarbodiimide (65.5 g, 0.33 mol) followed by 5-aminotetrazol monohydrate (36.6 g, 0.35 mol). The mixture was stirred for 24 hours at ambient temperature. The reaction volume was then reduced to one half by rotary evaporation, and water (800 mL) was added. The precipitate was collected by filtration, washed with cold acetonitrile and dried overnight in a vacuum oven to afford 46.0 g (80%) of 4-formyl-N-(2H-tetrazol-5-yl)benzamide.

Workup

  1. customThe reaction volume was then reduced to one half by rotary evaporation, and water (800 mL)
  2. additionwas added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with cold acetonitrile
  5. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-7a9268fe6d534dabb366961f3ec79cdf
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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