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

HRID 1578838Notes

Reaction equation

HRID 1578838 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 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-aminophenoxy)-3-n-butylamino-5-sulfamoylbenzoic acid of the formula ##SPC9##

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-be7658414bbd4d31bf177878b088a3a2
Source dataset
uspto-grants-1976_02
Patent number
US03939267

Reaction notes

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