Sodium Hydroxide → HCID 68133203, compound

HRID 1576717Notes

Reaction equation

HRID 1576717 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-3tolyloxy)-3benzylamino- 5-sulfamoylbenzoic acid and 25 ml of 2N aqueous sodium hydroxide is refluxed for 7 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 7 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-88e5202f68a941aeb9a638b5727bfc8a
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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