Water → 4-(DiethylcarbaMoyl)benzoic acid

HRID 1934768Notes

Reaction equation

HRID 1934768 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[OH-].[Na+].O.C(OCC)(=O)C>CO>[CH2:16]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:5])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 14434573Methyl 4-(diethylcarbamoyl)benzoate

Product 1

HCID 125534994-(DiethylcarbaMoyl)benzoic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 25 ml of methanol was dissolved 5.44 g of methyl 4-[(diethylamino)carbonyl]-benzoate. After adding 25 ml of 1 mol/L aqueous solution of sodium hydroxide at 0-5° C., the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into a mixture of water and ethyl acetate, and the aqueous layer was separated. The aqueous layer was mixed with ethyl acetate, pH was adjusted to 1.5 with 6 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the deposited crystal was collected by filtration to obtain 2.94 g of 4-[(diethylamino)carbonyl]-benzoic acid as a colorless crystalline product.

Workup

  1. customthe aqueous layer was separated
  2. additionThe aqueous layer was mixed with ethyl acetate, pH
  3. customthe organic layer was separated
  4. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-a73c6c33333040188faa9960f2a7505a
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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