Sulfacetamide → HCID 21862759, compound

HRID 1415826Notes

Reaction equation

HRID 1415826 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH:10]([CH3:13])[CH:11]=O)=O)=[CH:5][CH:4]=1.[C:16]([NH:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21])(=[O:18])[CH3:17].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[C:16]([NH:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([N:27]2[CH:11]=[C:10]([CH3:13])[CH:9]=[C:7]2[C:6]2[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21])(=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 5320SulfacetamideHCID 516892Sodium BicarbonateHCID 21862820HCID 21862820, compound

Product 1

HCID 21862759HCID 21862759, compoundYield 16.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2.82 g (12.8 mmol) of 3-(4-methoxybenzoyl)-2-methylpropionaldehyde [prepared as described in step (i) above] and 2.74 g (12.8 mmol) of 4-acetylaminosulfonylaniline in 30 ml of acetic acid was heated under reflux for 3 hours, after which the acetic acid was removed by distillation under reduced pressure. The residue thus obtained was dissolved in chloroform and a saturated aqueous solution of sodium hydrogencarbonate was added to the resulting solution to separate it into liquid phases. The organic extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 2:3 by volume mixture of hexane and ethyl acetate. It was then recrystallized from ethanol, to give 0.79 g (yield 16%) of the title compound as a white powder, melting at 215-217° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customafter which the acetic acid was removed by distillation under reduced pressure
  3. customThe residue thus obtained
  4. customto separate it into liquid phases
  5. extractionThe organic extract
  6. washwas washed with water and with a saturated aqueous solution of sodium chloride, in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationafter which it was concentrated by evaporation under reduced pressure
  9. customThe residue thus obtained
  10. washeluted with a 2:3 by volume mixture of hexane and ethyl acetate
  11. customIt was then recrystallized from ethanol

Sources & evidence

ORD record
ord-279ae9258ad4431dacd668991c0b7db1
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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