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

HRID 1649131Notes

Reaction equation

HRID 1649131 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-fe9241d55f4547ce8605df4ae1671be0
Source dataset
uspto-grants-1983_11
Patent number
US04415579

Reaction notes

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