Sodium Hydroxide → 4-(4-Aminophenoxy)-3-(butylamino)-5-sulfamoylbenzoic acid

HRID 1576710Notes

Reaction equation

HRID 1576710 reaction equation
C([NH:4][C:5]1[CH:29]=[CH:28][C:8]([O:9][C:10]2[C:18]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[NH:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>>[NH2:4][C:5]1[CH:29]=[CH:28][C:8]([O:9][C:10]2[C:18]([S:19](=[O:21])(=[O:22])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[NH:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54136254HCID 54136254, compound

Product 1

HCID 545033124-(4-Aminophenoxy)-3-(butylamino)-5-sulfamoylbenzoic acid

Procedure

The mixture of 1.9 g of 4-(4-acetamidophenoxy)-3-n-butylamino-5-sulfamoylbenzoic acid and 19 ml of 2N aqueous sodium hydroxide is refluxed for 1 hour under nitrogen. After cooling to room temperature it is filtered, the filtrate acidifed 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-aminophenoxy)-3-n-butylamino-5-sulfamoylbenzoic acid of the formula ##SPC9##

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-7f89c7dc1602448bb9cc12c461642c28
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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