Sulfanilamide → HCID 54299702, compound

HRID 1415772Notes

Reaction equation

HRID 1415772 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([CH2:8][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=O)=O)=[CH:4][CH:3]=1.[S:20]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)(=[O:23])(=[O:22])[NH2:21]>C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[N:28]([C:27]3[CH:29]=[CH:30][C:24]([S:20](=[O:23])(=[O:22])[NH2:21])=[CH:25][CH:26]=3)[CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5333SulfanilamideHCID 21862775HCID 21862775, compound

Product 1

HCID 54299702HCID 54299702, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.32 g (1.25 mmol) of 3-(4-fluorobenzoyl)-2-phenylpropionaldehyde [prepared as described in step (i) above] and 0.26 g (1.5 mmol) of 4-sulfamoylaniline were dissolved in 20 ml of acetic acid, and the mixture was heated under reflux for 4 hours. The solvent was then removed by distillation under reduced pressure and water was added to the residue, which was then extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was applied to a silica gel chromatography column and eluted with a 3:2 by volume mixture of hexane and ethyl acetate, to give 0.35 g (yield 60%) of the title compound as a slightly yellow powder, melting at 192-194° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent was then removed by distillation under reduced pressure and water
  4. additionwas added to the residue, which
  5. extractionwas then extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. washeluted with a 3:2 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-19595d0cb47a4e8eb1fa989dec538bd9
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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