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

HRID 1633929Notes

Reaction equation

HRID 1633929 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.O>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

5

Reactant 3

HCID 962WaterHCID 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 evapoation, 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. additionwas added
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with cold acetonitrile
  4. customdried overnight in a vacuum oven

Sources & evidence

ORD record
ord-95d986e64e594294ad66ada402cf9401
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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