m-Chloroperbenzoic acid → HCID 86038392, compound

HRID 2233872Notes

Reaction equation

HRID 2233872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12][CH3:13])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:13])=[O:22])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86038391Methyl 2-chloro-6-(methylthio)isonicotinate2×

Product 1

HCID 86038392HCID 86038392, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-chloro-6-(methylthio)isonicotinate (Intermediate 83; 290 mg), was dissolved in anhydrous DCM (5 ml). mCPBA (345 mg) was added and the mixture was stirred at room temperature for 90 minutes. The mixture was diluted with EtOAc and washed with water, 10% sodium thiosulfate, water, brine and dried over sodium sulfate. The mixture was concentrated in vacuo and purified by flash chromatography eluting with EtOAc:Hexane (7:3) to afford the title compound (129 mg).

Workup

  1. washwashed with water, 10% sodium thiosulfate, water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by flash chromatography
  5. washeluting with EtOAc:Hexane (7:3)

Sources & evidence

ORD record
ord-7654bb9416be43e4acd7bf3549d1ff06
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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