HCID 21563918, compound → HCID 21563913, compound

HRID 1580827Notes

Reaction equation

HRID 1580827 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:34])(=[O:33])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29]C(=O)C)=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:7][CH:6]=1)(=O)C>[OH-].[Na+]>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:34])(=[O:33])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH2:29])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[NH:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 21563918HCID 21563918, compound

Product 1

HCID 21563913HCID 21563913, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The mixture of 2 g of 4-(4-acetamidophenylamino)-3-benzylamino-5-(2-acetamidophenylsulfamoyl)-benzoic acid and 20 ml of 2 N aqueous sodium hydroxide is refluxed for 6 hours under nitrogen. After cooling to room temperature it is filtered, the filtrate acidified with glacial acetic acid to a pH of 4-5 and the precipitate formed filtered off. It is washed with water, taken up in 50 ml of 505 hot aqueous ethanol, the precipitate formed after cooling is filtered off and again recrystallized from 25 ml of 50% aqueous ethanol, to yield the 4-(4-aminophenylamino)-3-benzylamino-5-(2-aminophenylsulfamoyl)-benzoic acid of the formula ##SPC11##

Workup

  1. temperatureis refluxed for 6 hours under nitrogen
  2. filtrationis filtered
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. washIt is washed with water
  6. customthe precipitate formed
  7. temperatureafter cooling
  8. filtrationis filtered off
  9. customagain recrystallized from 25 ml of 50% aqueous ethanol

Sources & evidence

ORD record
ord-d105e29b91cf4d7c96095a295edc9d5a
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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