Hydrochloric Acid → 4-(4-Acetamidophenoxy)-3-nitro-5-sulfamoylbenzoic acid

HRID 1730411Notes

Reaction equation

HRID 1730411 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].[C:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)(=[O:20])[CH3:19].Cl>C(=O)(O)[O-].[Na+]>[C:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][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:24][CH:23]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1983AcetaminophenHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 214977894-(4-Acetamidophenoxy)-3-nitro-5-sulfamoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

The starting material is prepared as follows: The mixture of 14 g of 4-chloro-3-nitro-5-sulfamoylbenzoic acid, 200 ml of 1N aqueous sodium bicarbonate and 15.9 g of 4-acetamidophenol is heated to about 95°-100°C for 21 hours while stirring under nitrogen. It is cooled to room temperature and made strongly acidic with concentrated hydrochloric acid. The precipitate formed is filtered off, to yield the 4-(4-acetamidophenoxy)-3-nitro-5-sulfamoylbenzoic acid, which after trituration with aqueous ethanol melts at 293° with decomposition.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated to about 95°-100°C for 21 hours
  3. customThe precipitate formed
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-f911aa3769634cf5924932031aa06e9a
Source dataset
uspto-grants-1976_11
Patent number
US03992440

Reaction notes

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