HCID 21563899, compound → HCID 21563912, compound

HRID 1580825Notes

Reaction equation

HRID 1580825 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:20]([S:21](=[O:27])(=[O:26])[NH:22]C(=O)C)=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[CH2:28][CH:29]2[CH2:34][CH:33]3[CH2:35][CH:30]2[CH:31]=[CH:32]3)=[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:27])(=[O:26])[NH2:22])=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=2[CH2:28][CH:29]2[CH2:34][CH:33]3[CH2:35][CH:30]2[CH:31]=[CH:32]3)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 21563899HCID 21563899, compound

Product 1

HCID 21563912HCID 21563912, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The mixture of 5.1 g of 4-(4-acetamidophenylamino)-3-(2-norborn-5-enylmethyl)-5-acetylsulfamoylbenzoic acid and 50 ml of 2N aqueous sodium hydroxide is refluxed for 2 hours under nitrogen. It is cooled, 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, dissolved in 40 ml of hot ethanol, the solution filtered and the filtrate diluted with water. After standing the precipitate formed is filtered off and again recrystallized from aqueous ethanol, to yield the 4-(4-aminophenylamino)-3-(2-norborn-5-enylmethyl)-5-sulfamoylbenzoic acid of the formula ##SPC10##

Workup

  1. temperatureis refluxed for 2 hours under nitrogen
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. customthe precipitate formed
  5. filtrationfiltered off
  6. washIt is washed with water
  7. dissolutiondissolved in 40 ml of hot ethanol
  8. filtrationthe solution filtered
  9. additionthe filtrate diluted with water
  10. customformed
  11. filtrationis filtered off
  12. customagain recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-09df881e048e4afc91cd2e9d7bcaf814
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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