Hydrochloric Acid → 4-[(Dibenzylcarbamoyl)amino]benzoic acid

HRID 2166535Notes

Reaction equation

HRID 2166535 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[CH2:23]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1)=[O:10])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17381816Ethyl 4-[(dibenzylcarbamoyl)amino]benzoate

Product 1

HCID 204994724-[(Dibenzylcarbamoyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.61 g. of 1,1-dibenzyl-3-(4-carboethoxyphenyl)urea in 100 ml of ethanol is treated with 25 ml of 1 N aqueous sodium hydroxide solution, stirred under reflux for 16 hours, allowed to cool, acidified with 1 N hydrochloric acid, and filtered. The solid is recrystallized from ethanol to yield 1,1-dibenzyl-3-(4-carboxyphenyl)urea as a white solid, mp 210°-214°.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customThe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-1cbc0a9cda84493aa49faa1f0b93f3a7
Source dataset
uspto-grants-1983_06
Patent number
US04387106

Reaction notes

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