p-Chlorothiophenol → 2-{[(4-Chlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

HRID 2286219Notes

Reaction equation

HRID 2286219 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 129532882-{[(4-Chlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)Yield 170%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

4-Chlorobenzenethiol (5 g) in warm ethanol (5 ml) was added to a solution of sodium hydroxide (2.8 g) in ethanol (50 ml). To the solution was added a solution of 2-picolyl chloride, hydrochloride (5.7 g) in ethanol (25 ml) and the mixture was stirred at ambient temperature for 6 hours. The mixture was filtered and evaporated and the residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from ethanol-ether to give 2-(((4-chlorophenyl)thio)methyl)pyridine, hydrochloride (8 g) mp 196°-8° C. (Found: C,52.95; H,4.1; N,5.15 C12H10ClNS.HCl requires C,53.1; H,4.2; N,4.9%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customthis was recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-34c8cd5f9b2543ae8a9f4d10cab205d8
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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