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

HRID 1810156Notes

Reaction equation

HRID 1810156 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-8f9254788eef416e917b102d059579c9
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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