Sodium Hydroxide → HCID 54331480, compound

HRID 1730422Notes

Reaction equation

HRID 1730422 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S: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][C:27]2[O:31][CH:30]=[CH:29][CH:28]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S: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][C:27]2[O:31][CH:30]=[CH:29][CH:28]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54219533HCID 54219533, compound

Product 1

HCID 54331480HCID 54331480, compound

Procedure

The mixture of 2.3 g of 4-(4-acetamidophenylmercapto)-3-furfurylamino-5-sulfamoylbenzoic acid and 23 ml of 2N aqueous sodium hydroxide is refluxed for one hour under nitrogen. After cooling to room temperature it is acidified to pH = 5 and the precipitate formed filtered off. It is dissolved in 25 ml of 50% hot aqueous ethanol, the solution cooled to room temperature and decanted fromsome amorphous substance. The supernatant solution is allowed to stand at room temperature for a longer period of time, the precipitate formed filtered off and this recrystallization procedure repeated several times, to yield the 4-(4-aminophenylmercapto)-3-furfurylamino-5-sulfamoylbenzoic acid, starting to melt at about 125°.

Workup

  1. temperatureis refluxed for one hour under nitrogen
  2. customthe precipitate formed
  3. filtrationfiltered off
  4. dissolutionIt is dissolved in 25 ml of 50% hot aqueous ethanol
  5. temperaturethe solution cooled to room temperature
  6. customdecanted fromsome amorphous substance
  7. waitto stand at room temperature for a longer period of time
  8. customthe precipitate formed
  9. filtrationfiltered off
  10. customthis recrystallization procedure

Sources & evidence

ORD record
ord-d81896ad0b8f4090aad862756f54929f
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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