Gamma-Aminobutyric Acid → Butanoic acid, 4-(benzoylamino)-

HRID 1921662Notes

Reaction equation

HRID 1921662 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O>[C:10]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 37118Butanoic acid, 4-(benzoylamino)-Yield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.4 g of gamma-aminobutyric acid and 4.5 g of sodium hydroxide were dissolved in 100 mL of purified water, and 7.9 g of benzoyl chloride was dropwise added thereto under ice-cooling. After stirring the mixture for 6 hours, hydrochloric acid was added to adjust the pH to 2 or less. The precipitated crude product was filtered, and then recrystallized with ethanol solution to give 8.7 g of the desired product.

Workup

  1. temperatureunder ice-cooling
  2. customThe precipitated crude product
  3. filtrationwas filtered
  4. customrecrystallized with ethanol solution

Sources & evidence

ORD record
ord-bdf48983f8254f7ebce359772f7257cc
Source dataset
uspto-grants-2012_05
Patent number
US08173705B2

Reaction notes

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