Cesium carbonate → 2-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]-thio}-3-pyridinol

HRID 327139Notes

Reaction equation

HRID 327139 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1S[CH2:14][C:15](=O)[N:16]=1.SC1[C:30]([OH:31])=[CH:29]C=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1[C:30]([OH:31])=[CH:29][CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-oneHCID 178516238HCID 178516238, compound

Product 1

HCID 193788072-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]-thio}-3-pyridinol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Stir 300 mg. of the iodide prepared in Examples 2 or 3, 3 ml. acetonitrile 112 mg. 2-mercapto-3-pyridinol and 201 mg. cesium carbonate in a reaction flask overnight at room temperature. Remove the acetonitrile and add methylene chloride. Wash with sodium carbonate solution, water, then brine and dry over sodium sulfate. Remove the solvent then add methylene chloride, heat to dissolve the mixture, add hexane and cool to precipitate the title compound as white crystals.

Workup

  1. customovernight
  2. customat room temperature
  3. customRemove the acetonitrile
  4. additionadd methylene chloride
  5. washWash with sodium carbonate solution, water
  6. dry with materialbrine and dry over sodium sulfate
  7. customRemove the solvent
  8. temperatureadd methylene chloride, heat
  9. dissolutionto dissolve the mixture
  10. additionadd hexane
  11. temperaturecool
  12. customto precipitate the title compound as white crystals

Sources & evidence

ORD record
ord-e0b6e15f233248b582ca1b5bcf5e361f
Source dataset
uspto-grants-1993_12
Patent number
US05272167

Reaction notes

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