Potassium Carbonate → HCID 18472402, compound

HRID 565917Notes

Reaction equation

HRID 565917 reaction equation
[OH:1][CH:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:41])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[OH:1][CH:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N+:28]=1[O-:41])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 18472655HCID 18472655, compound

Product 1

HCID 18472402HCID 18472402, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (10ml) was dissolved (E)-N-[4-[hydroxy(2-pyridyl)methyl]phenyl]-3-(4-methylphenyl)cinnamamide (200mg), and to the mixture was added 70% mCPBA (152mg). The mixture was stirred at room temperature for 6 hours, and to the solution were added saturated sodium thiosulfate solution (10ml) and saturated potassium carbonate (10ml). The mixture was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give (E)-N-[4-[hydroxy(1-oxido-2-pyridyl)methyl]phenyl]-3-(4-methylphenyl)cinnamamide (Compound 80) (123mg) as colorless crystals.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-3c84101d44b94d9ebdd288386e9e7a7b
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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