Acetic Anhydride → HCID 21563919, compound

HRID 1580826Notes

Reaction equation

HRID 1580826 reaction equation
[C:1]([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[N+:25]([O-:27])=[O:26])=[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:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:23])(=[O:24])[NH:22][C:28](=[O:30])[CH3:29])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[N+:25]([O-:27])=[O:26])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 21563902HCID 21563902, compound

Product 1

HCID 21563919HCID 21563919, compound

Procedure

The starting material is prepared as follows: The mixture of 20 g of 4-(4-acetamidophenylamino)-3-nitro-5-sulfamoylbenzoic acid and 200 ml of acetic anhydride is refluxed for ten minutes while stirring under nitrogen. It is evaporated under reduced pressure, the residue triturated with water and dissolved in 200 ml of 2N aqueous sodium hydroxide. The solution is washed with diethyl ether, filtered and acidified with concentrated hydrochloric acid to pH of 1- and the precipitate filtered off, to yield the 4-(4-acetamidophenylamino)-3-nitro-5-acetylsulfamoylbenzoic acid melting at 175°-185°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for ten minutes
  3. customIt is evaporated under reduced pressure
  4. customthe residue triturated with water
  5. dissolutiondissolved in 200 ml of 2N aqueous sodium hydroxide
  6. washThe solution is washed with diethyl ether
  7. filtrationfiltered
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-d9adb73cd0a049eab607d34f1e4e661b
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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