Sulfuric Acid → 2,4-Dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoic acid

HRID 749484

Reaction equation

HRID 749484 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([NH:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[Cl:23])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].S(=O)(=O)(O)O>C(O)C>[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([NH:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[Cl:23])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69305912Ethyl 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoate

Product 1

HCID 687982672,4-Dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

120 mg (0.31 mmol) of ethyl 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoate were suspended in 6 ml of an ethanol/2 N sodium hydroxide solution mixture (1:1) and heated at 90° C. for 3 hours. After cooling to room temperature, the pH was adjusted to 2 with 2 N sulfuric acid, and the precipitate was filtered off with suction. 98 mg (88%) of the product were obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered off with suction

Sources & evidence

ORD record
ord-02347f89e7ff45a3bdaa4e3d85527075
Source dataset
uspto-grants-2008_07
Patent number
US07402674B2

Linked notes

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