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

HRID 1810145Notes

Reaction equation

HRID 1810145 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>>[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

3

Reactant 2

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

Product 1

HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chloride

Procedure

4-Chloro-3-sulfamoyl-benzoic acid (5 g) is treated with 20.5 mL of thionyl chloride and heated to reflux for 5.5 h. Thionyl chloride is removed and the residue is dried at 50° C. in vacuo to give 5.6 g of 4-chloro-3-sulfamoyl-benzoyl chloride as a tan powder. This material is taken up in 28 mL of methylene chloride and treated at 0° C. with 2.64 g of N,O-dimethylhydroxylamine hydrochloride followed by 10.9 mL of pyridine and stirred overnight at room temperature. The reaction mixture is quenched at 0° C. with 19 mL of 3 N aqueous HCl and extracted with ethyl acetate. The organics are combined, washed with saturated aqueous sodium bicarbonate, 0.1 N aqueous HCl and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The resulting crystals are filtered through a short pad of silica gel (1:2 hexanes/ethyl acetate) to give the title compound as a white powder. MS (m/z): (M−1) 277; Rf 0.36 (1:2 hexanes/ethyl acetate).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5.5 h
  3. customThionyl chloride is removed
  4. customthe residue is dried at 50° C. in vacuo

Sources & evidence

ORD record
ord-f05d22ae1c7c4bfcb4d3cd79cd0ce9ec
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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