Ammonium Hydroxide → 3-Sulfamoylbenzoic acid

HRID 655609Notes

Reaction equation

HRID 655609 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[OH-].[NH4+:15]>>[NH2:15][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 2293523-Sulfamoylbenzoic acidYield 96%

Procedure

To ice-cold solution of ammonium hydroxide (25%, 250 ml) is added 3-(chlorosulfonyl)benzoic acid (25 g, commercially available, Aldrich) portionwise and the mixture is stirred at room temperature for 15 h. The solvent is removed under vacuum to about 50 ml and the mixture is acidified with conc. HCl. The precipitate is collected by filtration and dried under vacuum to afford 22 g (96%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 13.44 (br s, 1H), 8.38 (s, 1H), 8.14 (d, J=7.5 Hz, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.72 (t, J=7.9 Hz, 1H), 7.49 (s, 2H), HPLC (max plot) 97%; Rt 0.68 min. LC/MS: (ES−): 199.8.

Workup

  1. customThe solvent is removed under vacuum to about 50 ml
  2. filtrationThe precipitate is collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-dd321d2be9944376b563ee58e45c0724
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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