Thiophenol → 2-[(Phenylsulfanyl)methyl]pyridine--hydrogen chloride (1/1)

HRID 1156763Notes

Reaction equation

HRID 1156763 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Cl.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][Cl:17]>C(O)C>[ClH:17].[C:1]1([S:7][CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 23392Picolyl chloride hydrochlorideHCID 5360545Sodium

Product 1

HCID 124744352-[(Phenylsulfanyl)methyl]pyridine--hydrogen chloride (1/1)Yield 5.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiophenol (21 ml) was added to a solution of sodium (4.6 g) in ethanol (100 ml). To the resulting solution was added 2-picolyl chloride, hydrochloride (15 g) and the mixture was heated at reflux for 2 hours. Precipitated sodium chloride was removed by filtration and the solution was acidified with ethereal HCl. The solvent was removed by evaporation and the residue induced to crystallise by trituration with ether. Recrystallisation from ethanol-ether gave 2-((phenylthio)methyl)pyridine, hydrochloride (5.0 g) mp 142°-4° C. (Found: C, 60.6; H, 5.25; N, 5.5. C12H11NS, HCl requires C, 60.6; H, 5.1; N, 5.9%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customPrecipitated sodium chloride was removed by filtration
  4. customThe solvent was removed by evaporation
  5. customthe residue induced to crystallise by trituration with ether
  6. customRecrystallisation from ethanol-ether

Sources & evidence

ORD record
ord-ed4f0ec217ab461c92c10a6121a781c1
Source dataset
uspto-grants-1982_06
Patent number
US04337259

Reaction notes

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