Ethanol → Benzoic acid, 3-(aminosulfonyl)-4-chloro-, ethyl ester

HRID 873612Notes

Reaction equation

HRID 873612 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[CH2:15](O)[CH3:16]>>[CH2:15]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([S:11](=[O:13])(=[O:14])[NH2:12])[CH:4]=1)[CH3:16]

Participants

3

Reactant 2

HCID 702EthanolHCID 145684-Chloro-3-sulfamoylbenzoic acid

Product 1

HCID 15938945Benzoic acid, 3-(aminosulfonyl)-4-chloro-, ethyl esterYield 99%

Procedure

To a suspension of 4-chloro-3-sulfamoyl-benzoic acid (50 g, 212 mmol) in 500 mL ethanol is bubbled HCl gas for 10 minutes. The resulting suspension is then heated at reflux for 16 h, cooled and concentrated in vacuo. The resulting residue is recrystallized from isopronanol to yield 55.9 g (99%) of the title compound as an off-white solid.

Workup

  1. customis bubbled HCl gas for 10 minutes
  2. temperatureThe resulting suspension is then heated
  3. temperatureat reflux for 16 h
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is recrystallized from isopronanol

Sources & evidence

ORD record
ord-b028dd31e38643a491ec6c5dc46c772d
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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