Acetic Anhydride → 4-(4-Acetamidophenoxy)-3-nitro-5-acetylsulfamoylbenzoic acid

HRID 1578848Notes

Reaction equation

HRID 1578848 reaction equation
[C:1]([NH:4][C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:18]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[N+:23]([O-:25])=[O:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[C:1]([NH:4][C:5]1[CH:27]=[CH:26][C:8]([O:9][C:10]2[C:18]([S:19](=[O:21])(=[O:22])[NH:20][C:28](=[O:30])[CH3:29])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=2[N+:23]([O-:25])=[O:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 214977894-(4-Acetamidophenoxy)-3-nitro-5-sulfamoylbenzoic acid

Product 1

HCID 214977944-(4-Acetamidophenoxy)-3-nitro-5-acetylsulfamoylbenzoic acid

Procedure

The starting material is prepared as follows: The mixture of 12.5 g of 4-(4-acetamidophenoxy)-3-nitro-5-sulfamoylbenzoic acid and 125 ml of acetic anhydride is refluxed for two hours under nitrogen and evaporated under reduced pressure. The residue is taken up in 125 ml of 2N aqueous sodium hydroxide and 25 ml of water, the solution washed with diethyl ether, filtered and the filtrate acidified with concentrated hydrochloric acid and the precipitate recrystallized from 33 and 50% aqueous ethanol, to yield the 4-(4-acetamidophenoxy)-3-nitro-5-acetylsulfamoylbenzoic acid decomposing at about 240°. The solution of 10.5 g thereof in 100 ml of water and 22 ml of 2N aqueous sodium hydroxide is hydrogenated over 2.5 g of 10% palladium on charcoal until the theoretical amount of hydrogen has been absorbed. The mixture is filtered, the filtrate acidified with concentrated hydrochloric acid and the precipitate recrystallized from aqueous ethanol, to yield the 4-(4-acetamidophenoxy)-3-amino-5-acetylsulfamoylbenzoic acid melting at 305°-306° with decomposition.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for two hours under nitrogen
  3. customevaporated under reduced pressure
  4. wash25 ml of water, the solution washed with diethyl ether
  5. filtrationfiltered
  6. customthe precipitate recrystallized from 33 and 50% aqueous ethanol

Sources & evidence

ORD record
ord-f39e8976c94348b799bcfbc3c4e20b50
Source dataset
uspto-grants-1976_02
Patent number
US03939267

Reaction notes

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