Hydrochloric Acid → 3-(3-chloro-benzenesulfonylamino)-benzoic acid

HRID 2241163Notes

Reaction equation

HRID 2241163 reaction equation
C([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)(=[O:14])=[O:13])[CH:6]=1)C.[OH-].[K+].Cl>C(O)C>[Cl:21][C:17]1[CH:16]=[C:15]([S:12]([NH:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:22])=[O:3])(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 8823771HCID 8823771, compound

Product 1

HCID 81909843-(3-chloro-benzenesulfonylamino)-benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(3-chloro-benzenesulfonylamino)-benzoic acid ethyl ester (4.03 g, 12.0 mmol) in ethanol (20.0 ml) was treated with 3N KOH (12.0 ml) and stirred at room temperature overnight. The mixture was then acidified with 3N HCl and the resulting slurry cooled to 0° C. The precipitated solid was filtered, washing with ethanol and dried under vacuum, yielding 3-(3-chloro-benzenesulfonylamino)-benzoic acid (2.61 g, 70%) as an off-white solid, MS (ISP): m/e=310.0 (M−H).

Workup

  1. temperaturethe resulting slurry cooled to 0° C
  2. filtrationThe precipitated solid was filtered
  3. washwashing with ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e85edeec82aa4a68ae6f158bd5e556a2
Source dataset
uspto-grants-2010_05
Patent number
US07723538B2

Reaction notes

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