Thiophenol → 2-((Phenylthio)methyl)pyridine

HRID 72639

Reaction equation

HRID 72639 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+].Cl[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CN(C=O)C>[C:1]1([S:7][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 23393Picolyl chlorideHCID 25953Cesium fluoride

Product 1

HCID 1944222-((Phenylthio)methyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Thiophenol 2(2) (2.77 g, 0.025 mol), cesium carbonate (24.65 g, 0.075 mol) and catalytical amount of cesium fluoride were added successively to a solution of 2-chloromethylpyridine 6(1) (1.13 g, 0.017 mol) in absolute DMF (28 ml). The reaction mixture was stirred at 50-60° C. for 2 h in argon current and left for night at 20° C. Solvent was removed in vacuo, the residue was dissolved in water, the reaction product was extracted with CH2Cl2, dried over MgSO4, solvent was evaporated in vacuo. It gave 2-phenylsulphanylmethylpyridine 6(2), 3.2 g, (95%).

Workup

  1. waitleft for night at 20° C
  2. customSolvent was removed in vacuo
  3. dissolutionthe residue was dissolved in water
  4. extractionthe reaction product was extracted with CH2Cl2
  5. dry with materialdried over MgSO4, solvent
  6. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-732657db7ea443d1bfa53512ad456a36
Source dataset
uspto-grants-2014_09
Patent number
US08829002B2

Linked notes

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