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

HRID 1576712Notes

Reaction equation

HRID 1576712 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 1 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 1 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-5ccfb26ba387415eba220d10abb0d46b
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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