HCID 54064894, compound → HCID 21563921, compound

HRID 1580830Notes

Reaction equation

HRID 1580830 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[NH:22][CH2:23][C:24]2[O:28][CH:27]=[CH:26][CH:25]=2)=[CH:4][CH:3]=1>[Pd].O1CCOCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:17]([S:18](=[O:20])(=[O:21])[NH2:19])=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[NH:22][CH2:23][CH:24]2[CH2:25][CH2:26][CH2:27][O:28]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54064894HCID 54064894, compound

Product 1

HCID 21563921HCID 21563921, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The mixture of 1.2 g of 4-(4-aminophenylamino)-3-furfurylamino-5-sulfamoylbenzoic acid (Example 3), 0.6 g of 10% palladium on charcoal and 120 ml of dioxane is hydrogenated at room temperature and atmospheric pressure until the theoretical amount of hydrogen has been absorbed (about 2 hours). It is filtered, the filtrate evaporated under reduced pressure, the residue is triturated with water, dissolved in 40 ml of 50% hot aqueous ethanol, the solution filtered hot, the filtrate cooled and the precipitate formed filtered off, to yield the 4-(4-aminophenylamino)-3-(2-tetrahydrofurylmethylamino)-5-sulfamoylbenzoic acid, melting at 253° with decomposition.

Workup

  1. customis hydrogenated at room temperature
  2. customatmospheric pressure until the theoretical amount of hydrogen has been absorbed (about 2 hours)
  3. filtrationIt is filtered
  4. customthe filtrate evaporated under reduced pressure
  5. customthe residue is triturated with water
  6. dissolutiondissolved in 40 ml of 50% hot aqueous ethanol
  7. filtrationthe solution filtered hot
  8. temperaturethe filtrate cooled
  9. customthe precipitate formed
  10. filtrationfiltered off

Sources & evidence

ORD record
ord-8f07944fd33f42529ea232df07247e2c
Source dataset
uspto-grants-1976_01
Patent number
US03933906

Reaction notes

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