m-Chloroperbenzoic acid → HCID 18472669, compound

HRID 2228159Notes

Reaction equation

HRID 2228159 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:16])=[CH:10][CH:9]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>O1CCCC1>[O-:42][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]([C:17]2[CH2:18][O:19][C:20]3[CH:26]=[CH:25][C:24]([C:27]4[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=4)=[CH:23][C:21]=3[CH:22]=2)=[O:16])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18472627HCID 18472627, compound

Product 1

HCID 18472669HCID 18472669, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4—(2-pyridylmethyl)phenyl]-6—(4-methylphenyl)-2H-1-benzopyran-3-carboxamide (250 mg) in tetrahydrofuran (10 ml) was added 3-chloroperbenzoic acid (70%, 0.21 g) at 0° C., and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was added sodiumithiosulfate solution, and the mixture was stirred for a few minutes. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:3) concentrated to give crystals, which were recrystallized from chloroform-ethanol to give N-[4—(1-oxidopyridin-2-ylmethyl)phenyl]-6—(4-methylphenyl)-2H-1-benzopyran-3-carboxamide (Compound 200) (191 mg) as pale yellow crystals.

Workup

  1. additionTo the reaction mixture was added sodiumithiosulfate solution
  2. stirringthe mixture was stirred for a few minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified with column chromatography (ethanol/ethyl acetate=1:3)
  9. concentrationconcentrated
  10. customto give crystals, which
  11. customwere recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-1257269c8c4e47e69a230b8a482c3296
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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