Benzyl mercaptan → 2-Benzylthio-3-iodopyridine

HRID 1901254

Reaction equation

HRID 1901254 reaction equation
F[C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([SH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:9]([S:16][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 70095012-Fluoro-3-iodopyridine

Product 1

HCID 150368652-Benzylthio-3-iodopyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 34.0 g (0.15 mol) of 2-fluoro-3-iodopyridine and 18.6 g (0.15 mol) of benzylmercaptan in 250 ml of acetonitrile is heated under reflux with 22.8 g (0.165 mol) of potassium carbonate for 8 h. The mixture is cooled, the solvent is removed on a rotary evaporator, the residue is taken up in dichloromethane and the organic phase is washed with water. After drying with sodium sulfate, evaporating and distilling the oily residue in vacuo, 37.3 g (76% of theory) of 2-benzylthio-3-iodopyridine of boiling point 150°-153° C. at 0.1 mbar are obtained.

Workup

  1. temperatureThe mixture is cooled
  2. customthe solvent is removed on a rotary evaporator
  3. washthe organic phase is washed with water
  4. dry with materialAfter drying with sodium sulfate
  5. customevaporating
  6. distillationdistilling the oily residue in vacuo, 37.3 g (76% of theory) of 2-benzylthio-3-iodopyridine of boiling point 150°-153° C. at 0.1 mbar
  7. customare obtained

Sources & evidence

ORD record
ord-a8e62dedc8184f9097134e822495b6bc
Source dataset
uspto-grants-1996_11
Patent number
US05576440

Linked notes

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