Sodium Hydroxide → 4-[(4-Aminophenyl)sulfanyl]-3-(butylamino)-5-sulfamoylbenzoic acid

HRID 1730412Notes

Reaction equation

HRID 1730412 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54252021HCID 54252021, compound

Product 1

HCID 542886564-[(4-Aminophenyl)sulfanyl]-3-(butylamino)-5-sulfamoylbenzoic acid

Procedure

The mixture of 2.8 g of 4-(4-acetamidophenylmercapto)-3-n-butylamino-5-sulfamoylbenzoic acid and 28 ml of 2N aqueous sodium hydroxide is refluxed for one hour under nitrogen. After cooling to room temperature it is filtered, the filtrate acidified with glacial acetic acid to a pH of 4-5, the precipitate formed filtered off, washed with water and recrystallized from 50% aqueous ethanol, to yield the 4-(4-aminophenylmercapto)-3-n-butylamino-5-sulfamoylbenzoic acid of the formula ##SPC11##

Workup

  1. temperatureis refluxed for one hour under nitrogen
  2. filtrationis filtered
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. washwashed with water
  6. customrecrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-54f8eb838d2047c485637fb848bb04c7
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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