Furfural → HCID 54430759, compound

HRID 1578854Notes

Reaction equation

HRID 1578854 reaction equation
[O:1]([C:8]1[C:16]([S:17](=[O:30])(=[O:29])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26](=[O:28])[CH3:27])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[NH2:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:32](=O)[C:33]1[O:37][CH:36]=[CH:35][CH:34]=1>>[O:1]([C:8]1[C:16]([S:17](=[O:30])(=[O:29])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26](=[O:28])[CH3:27])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[NH:31][CH2:32][C:33]1[O:37][CH:36]=[CH:35][CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7362FurfuralHCID 21558938HCID 21558938, compound

Product 1

HCID 54430759HCID 54430759, compound

Procedure

The starting material is prepared as follows: The mixture of 3.5 g of 4-phenoxy-3-amino-5-(2-acetamidophenylsulfamoyl)-benzoic acid and 30 ml of furfural is heated to 100° for five hours and allowed to stand at room temperature for 16 hours. It is evaporated under reduced pressure, the residue triturated with diethyl ether and dissolved in 75 ml of ethanol. Thereupon 2 g of sodium borohydride are added while stirring and cooling followed by another 0.5 g thereof after 4 hours and another 0.5 g thereof after 16 hours and stirring is continued for one hour. Thereupon 100 ml of water are added, the mixture filtered and the filtrate acidified with hydrochloric acid to a pH of 2-3. The precipitate formed is filtered off and recrystallized from 30% aqueous ethanol to yield the 4-phenoxy-3-furfurylamino-5-(2-acetamidophenylsulfamoyl)-benzoic acid melting at 207°-210° with decomposition.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated to 100° for five hours
  3. customIt is evaporated under reduced pressure
  4. customthe residue triturated with diethyl ether
  5. dissolutiondissolved in 75 ml of ethanol
  6. additionThereupon 2 g of sodium borohydride are added
  7. temperaturecooling
  8. waitafter 4 hours
  9. waitanother 0.5 g thereof after 16 hours
  10. stirringstirring
  11. waitis continued for one hour
  12. additionThereupon 100 ml of water are added
  13. filtrationthe mixture filtered
  14. customThe precipitate formed
  15. filtrationis filtered off
  16. customrecrystallized from 30% aqueous ethanol

Sources & evidence

ORD record
ord-b77d95e30d534825afe4f69f15bf2656
Source dataset
uspto-grants-1976_02
Patent number
US03939267

Reaction notes

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