5-Acetylsalicylic acid → 2-Hydroxy-5-[1-oxo-3-[4-[(2-pyridinylamino)sulfonyl]phenyl]-2-propenyl]benzoic acid

HRID 1464177Notes

Reaction equation

HRID 1464177 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=O.[C:19]([C:22]1[CH:23]=[CH:24][C:25]([OH:31])=[C:26]([CH:30]=1)[C:27]([OH:29])=[O:28])(=[O:21])[CH3:20]>[OH-].[Na+].O.C(O)(=O)C>[OH:31][C:25]1[CH:24]=[CH:23][C:22]([C:19](=[O:21])[CH:20]=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)(=[O:11])=[O:10])=[CH:5][CH:4]=2)=[CH:30][C:26]=1[C:27]([OH:29])=[O:28]

Participants

6

Reactant 2

HCID 831515-Acetylsalicylic acidHCID 194233934-Formyl-N-(2-pyridinyl)benzenesulfonamide

Product 1

HCID 542873792-Hydroxy-5-[1-oxo-3-[4-[(2-pyridinylamino)sulfonyl]phenyl]-2-propenyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Formyl-N-(2-pyridinyl)benzenesulfonamide (5.7 g, 0.022 mol), 5-acetyl-2-hydroxybenzoic acid (6.64 g, 0.044 mol) in 5M sodium hydroxide (20 ml) were stirred for 3 days at room temperature. The solution was diluted with water (100 ml) and acetic acid added dropwise in excess. The precipitate was collected by filtration and washed with water. After drying, the material was recrystallized from acetic acid and dried at 120° C. in vacuo. Yield 6.4 g, 66%.

Workup

  1. additionadded dropwise in excess
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customAfter drying
  5. customthe material was recrystallized from acetic acid
  6. customdried at 120° C. in vacuo

Sources & evidence

ORD record
ord-f20e399c48754e5bbc8c1c163cdc0fe3
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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