Thionyl Chloride → 4-Methyl-3-sulfamoyl-benzoyl chloride

HRID 873628Notes

Reaction equation

HRID 873628 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].S(Cl)([Cl:17])=O>>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:17])=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2395854-Methyl-3-sulfamoylbenzoic acid

Product 1

HCID 227605604-Methyl-3-sulfamoyl-benzoyl chloride

Procedure

4-Methyl-3-sulfamoyl-benzoic acid (2 g, 10 mmol) is added to thionyl chloride (15 mL) and heated at reflux for 3 hours. Hexanes are added to the cooled solution and an oil forms. The hexanes are decanted and the oil is dissolved in methylene chloride and washed with hexanes. The solvent is removed under reduced pressure and the crude oil used in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customThe hexanes are decanted
  4. dissolutionthe oil is dissolved in methylene chloride
  5. washwashed with hexanes
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7d1f57d7de504e8e98d7ed873e175b67
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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