Benzamide → Hippuric Acid

HRID 1763089Notes

Reaction equation

HRID 1763089 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:13][C:14]([O-:16])=[O:15].[Na+]>CN(C)C=O>[C:14]([OH:16])(=[O:15])[CH2:13][NH:9][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 2331BenzamideHCID 14797Potassium HydroxideHCID 23675628Sodium bromoacetate

Product 1

HCID 464Hippuric AcidYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 150 ml of N,N-dimethylformamide, were added 24 g of benzamide, 14 g of potassium hydroxide and 40 g of sodium bromoacetate. They were reacted at 60° C. for 4 hours with stirring. After the reaction, the reaction solution was treated in the same manner as in Example 65. The resulting distillation residue was recrystallized from distilled water, thereby obtaining 34 g of hippuric acid having a melting point of 187° C.(yield: 69%).

Workup

  1. customThey were reacted at 60° C. for 4 hours
  2. customAfter the reaction
  3. additionthe reaction solution was treated in the same manner as in Example 65
  4. distillationThe resulting distillation residue
  5. customwas recrystallized
  6. distillationfrom distilled water

Sources & evidence

ORD record
ord-578c605a401849b6b0a46b9b99b9abd6
Source dataset
uspto-grants-1989_05
Patent number
US04835312

Reaction notes

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