Furfural → HCID 54219533, compound

HRID 1576723Notes

Reaction equation

HRID 1576723 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S: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[NH2:25])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH:26](=O)[C:27]1[O:31][CH:30]=[CH:29][CH:28]=1>COCCOCCOC>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S: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[NH:25][CH2:26][C:27]2[O:31][CH:30]=[CH:29][CH:28]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7362FurfuralHCID 54216006HCID 54216006, compound

Product 1

HCID 54219533HCID 54219533, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

The starting material is prepared as follows: The mixture of 2 g of 4-(4-acetamidophenylmercapto)-3-amino-5-sulfamoylbenzoic acid, 1 g of furfural and 20 ml of diethyleneglycol dimethyl ether is heated to 105° for 22 hours while stirring under nitrogen. It is evaporated under reduced pressure, the residue taken up in 75 ml of ethanol and 1 g of sodium borohydride is added portionwise while stirring at room temperature under nitrogen. After stirring overnight, 75 ml of water are added and the mixture is filtered. The filtrate is concentrated under reduced pressure, the concentrate acidified with concentrated hydrochloric acid and the precipitate formed filtered off, to yield the 4-(4-acetamidopheylmercapto)-3-furfurylamino-5-sulfamoylbenzoic acid.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated to 105° for 22 hours
  3. customIt is evaporated under reduced pressure
  4. addition1 g of sodium borohydride is added portionwise
  5. stirringwhile stirring at room temperature under nitrogen
  6. stirringAfter stirring overnight
  7. addition75 ml of water are added
  8. filtrationthe mixture is filtered
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. customthe precipitate formed
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-e077a5a5b9c74f3c9500bdbab0387cb0
Source dataset
uspto-grants-1976_09
Patent number
US03982018

Reaction notes

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