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

HRID 1810140Notes

Reaction equation

HRID 1810140 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-dfd5e6aea49544119d890f0acd9b7ec5
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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