Methyl 2,6-dichloroisonicotinate → HCID 87586921, compound

HRID 732465Notes

Reaction equation

HRID 732465 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([Cl:11])[CH:5]=1.[S-][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].[S:21]([O-:26])(O[O-])(=O)=[O:22].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([Cl:11])[N:7]=[C:8]([S:21]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:26])=[O:22])[CH:9]=1

Participants

5

Reactant 3

HCID 93237Methyl 2,6-dichloroisonicotinateHCID 4110039Sodium benzenethiolateHCID 10313463Potassium peroxymonosulphate

Product 1

HCID 87586921HCID 87586921, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix 2,6-dichloro-isonicotinic acid methyl ester (1 g, 4.85 mmol) and sodium thiophenoxide (0.64 g, 4.85 mmol) in DMF (10 mL) at room temperature for 4 h. Quench with water and extract with dichloromethane. Dry the dichloromethane layer over magnesium sulfate and concentrate. Dissolve the residue in chloroform (30 mL) and add neutral alumina (6 g) and potassium peroxymonosulfate (11.92 g, 19.39 mmol). Reflux for 16 h, concentrate and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes) to give the title compound as a white solid (1.4 g, 93%).

Workup

  1. customQuench with water
  2. extractionextract with dichloromethane
  3. dry with materialDry the dichloromethane layer over magnesium sulfate
  4. concentrationconcentrate
  5. dissolutionDissolve the residue in chloroform (30 mL)
  6. temperatureReflux for 16 h
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-93ec236c34324f3081a3b2e02194eb74
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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