Sulfuric Acid → 4-Chloro-2-fluoro-5-sulfamoylbenzoic acid

HRID 1599102Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](Cl)(Cl)Cl)=[C:4]([F:12])[CH:3]=1.[OH:13][S:14](Cl)(=O)=[O:15].S(=O)(=O)(O)[OH:19].[OH-:23].[NH4+:24]>>[Cl:1][C:2]1[C:7]([S:14](=[O:15])(=[O:13])[NH2:24])=[CH:6][C:5]([C:8]([OH:19])=[O:23])=[C:4]([F:12])[CH:3]=1

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 14923Ammonium Hydroxide

HCID 24638Chlorosulfonic acid

HCID 189316154-Chloro-2-fluoro-1-(trichloromethyl)benzene

Product 1

HCID 124625724-Chloro-2-fluoro-5-sulfamoylbenzoic acid

Procedure

4-chloro-2-fluoro-benzotrichloride (III) obtained in step (A) is chlorosulfonylated by treatment with sulfuric chlorohydrin in the presence of sulfuric acid and the resulting product is ammonolyzed by treatment with ammonium hydroxide to give 4-chloro-2-fluoro-5-sulfamoyl-benzoic acid (IV);

Sources & evidence

ORD record: ord-0e15f147aa2947928872a1644447127e
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739361

Reaction notes

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