Sodium Hydroxide → 4-[(4-Acetamidophenyl)sulfanyl]-3-nitro-5-sulfamoylbenzoic acid

HRID 1730413Notes

Reaction equation

HRID 1730413 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[OH-].[Na+].[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([SH:30])=[CH:26][CH:25]=1)(=[O:22])[CH3:21]>>[C:20]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([S:30][C:2]2[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])=[CH:26][CH:25]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 707774'-MercaptoacetanilideHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 541413694-[(4-Acetamidophenyl)sulfanyl]-3-nitro-5-sulfamoylbenzoic acid

Procedure

The starting material is prepared as follows: The mixture of 19.6 g of 4-chloro-3-nitro-5-sulfamoylbenzoic acid, 280 ml of N aqueous sodium hydroxide and 11.8 g of 4-acetamidothiophenol is stirred for 24 hours at room temperature under nitrogen. It is filtered, the filtrate made strongly acidic with concentrated hydrochloric acid, the precipitate formed filtered off and recrystallized from 50% aqueous ethanol, to yield the 4-(4-acetamidophenylmercapto)-3-nitro-5-sulfamoylbenzoic acid, meltingat 168°.

Workup

  1. customThe starting material is prepared
  2. filtrationIt is filtered
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. customrecrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-b01bf4df05584b9c9810231a45fc8226
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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