Sodium Hydroxide → HCID 68133203, compound

HRID 1730417Notes

Reaction equation

HRID 1730417 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[O:12][C:13]1[C:21]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)C.[OH-].[Na+]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[O:12][C:13]1[C:21]([S:22](=[O:24])(=[O:25])[NH2:23])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[NH:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 68133124HCID 68133124, compound

Product 1

HCID 68133203HCID 68133203, compound

Procedure

The mixture of 2.5 g of 4-(4-acetamido-3-tolyloxy)-3-benzylamino-5-sulfamoylbenzoic acid and 25 mlof 2N aqueous sodium hydroxide is refluxed for seven hours under nitrogen. After cooling it is filtered, the filtrate acidified to a pH of 4-5 with glacial acetic acid, the precipitate formed filtered off, washed with water and recrystallized from 50% aqueous ethanol, to yield the 4-(4-amino-3-tolyloxy)-3-benzylamino-5-sulfamoylbenzoic acid of the formula ##SPC13##

Workup

  1. temperatureis refluxed for seven hours under nitrogen
  2. temperatureAfter cooling it
  3. filtrationis filtered
  4. customthe precipitate formed
  5. filtrationfiltered off
  6. washwashed with water
  7. customrecrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-303bfce00381487b924913ce7786113a
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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