Potassium Hydroxide → 4-chloro-3-((trifluoromethyl)phenyl)-N'-(4-carboxyphenyl)urea

HRID 78338Notes

Reaction equation

HRID 78338 reaction equation
[Cl:1][C:2]1([C:22]([O:24]CC)=[O:23])[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:9](=[O:11])[NH2:10])=[CH:4][CH2:3]1.[OH-].[K+]>CO>[Cl:1][C:2]1([C:22]([OH:24])=[O:23])[CH:3]=[CH:4][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])[C:9](=[O:11])[NH2:10])=[CH:6][CH2:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 865836154-chloro-3-((trifluoromethyl)phenyl)-N'-(4-ethoxycarbonylphenyl)urea

Product 1

HCID 865836144-chloro-3-((trifluoromethyl)phenyl)-N'-(4-carboxyphenyl)ureaYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-ethoxycarbonylphenyl)urea (Method C1e; 5.93 g, 15.3 mmol) in MeOH (75 mL) was added an aqueous KOH solution (2.5 N, 10 mL, 23 mmol). The resulting mixture was heated at the reflux temp. for 12 h, cooled to room temp., and concentrated under reduced pressure. The residue was diluted with water (50 mL), then treated with a 1 N HCl solution to adjust the pH to 2 to 3. The resulting solids were collected and dried under reduced pressure to give N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-carboxyphenyl)urea as a white solid (5.05 g, 92%).

Workup

  1. temperatureThe resulting mixture was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with water (50 mL)
  5. additiontreated with a 1 N HCl solution
  6. customThe resulting solids were collected
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-f32fa6393e874f76a37ef57c3ffd8e34
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Reaction notes

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