4-Chloro-3-sulfamoylbenzoic acid → 3-(Aminosulfonyl)-4-chlorobenzoyl chloride

HRID 1515410Notes

Reaction equation

HRID 1515410 reaction equation
[Cl: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>CCCCCC>[Cl: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

4

Reactant 2

HCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideYield 97.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 4-chloro-3-sulfamoyl-benzoic acid (50 g, 212 mmol) and thionyl chloride (31 mL, 424 mmol) are heated to reflux for 5 h then allowed to cool to room temperature. To this mixture is added hexane and the resulting solid is filtered, washed with hexane and dried in vacuo to yield 52.3 g (97%) of the title compound as an off-white solid.

Workup

  1. temperatureare heated
  2. temperatureto reflux for 5 h
  3. filtrationthe resulting solid is filtered
  4. washwashed with hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ec13b7212e7c4db6b6c0117151c9cab9
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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