HCID 54140222, compound → HCID 54507843, compound

HRID 1580819Notes

Reaction equation

HRID 1580819 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH: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]([NH:11][C:12]2[C:20]([S:21](=[O:23])(=[O:24])[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 1

HCID 54140222HCID 54140222, compound

Product 1

HCID 54507843HCID 54507843, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The mixture of 2 g of 4-(4-acetamidophenylamino)-3-n-butylamino-5-sulfamoylbenzoic acid and 50 ml of 2N aqueous sodium hydroxide is refluxed for one hour under nitrogen. It is cooled, filtered and the filtrate acidified with glacial acetic acid to a pH of 4-5. The mixture is cooled in an ice bath, the precipitate formed filtered off and recrystallized from 50% aqueous ethanol, to yield the 4-(4-aminophenylamino)-3-n-butylamino-5-sulfamoylbenzoic acid of the formula ##SPC8##

Workup

  1. temperatureis refluxed for one hour under nitrogen
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. temperatureThe mixture is cooled in an ice bath
  5. customthe precipitate formed
  6. filtrationfiltered off
  7. customrecrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-873a5e5c4ada4aa4b9f3c27093dd0841
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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