2,6-Dichloropyridine → HCID 63585999, compound

HRID 1626449Notes

Reaction equation

HRID 1626449 reaction equation
[CH3:1][C:2]([S-:5])([CH3:4])[CH3:3].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Cl)[N:9]=1>CN(C=O)C.C(OCC)(=O)C>[C:2]([S:5][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[N:9]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 169892,6-DichloropyridineHCID 5147913Sodium 2-methyl-2-propanethiolate

Product 1

HCID 63585999HCID 63585999, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of sodium 2-methylpropane-2-thiolate (188 mg, 1.68 mmol) in DMF was treated with 2,6-dichloropyridine (4865 μl, 1.46 mmol) at ambient temperature in a vial. The vial was capped and heated to 80° C. with rapid stirring of the colorless solution. After 12 hours, the reaction was cooled to ambient temperature and diluted with ethyl acetate. The ethyl acetate solution was washed with brine solution, dried with sodium sulfate, filtered, concentrated and purified on silica gel. Elution with 2% to 10% ethyl acetate/hexanes provided the title compound (271 mg, 1.34 mmol, 92.0% yield) as a light yellow oil.

Workup

  1. customThe vial was capped
  2. temperaturethe reaction was cooled to ambient temperature
  3. washThe ethyl acetate solution was washed with brine solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel
  8. washElution with 2% to 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-edbd239d98f140c9829df32754dc03ce
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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