Benzenethiol, pentafluoro- → 2-{[(Pentafluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

HRID 2286225Notes

Reaction equation

HRID 2286225 reaction equation
[F:1][C:2]1[C:7]([SH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[OH-].[Na+].Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][Cl:23]>C(O)C>[ClH:23].[F:1][C:2]1[C:7]([S:8][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=2)=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12]

Participants

5

Reactant 3

HCID 13042Benzenethiol, pentafluoro-HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochloride

Product 1

HCID 127602242-{[(Pentafluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)Yield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Pentafluorothiophenol (5 g) was added to a solution of sodium hydroxide (2.0 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.1 g) in ethanol (25 ml). The mixture was stirred at ambient temperature for 4 hours, filtered through Kieselghur and the solvent removed by evaporation. The residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from acetone-ether to give 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (5.0 g) mp 157°-8° C. (Found: C,44.0; H,2.4; N,4.0; C12H6F5NS.HCl requires C,44.0; H,2.15; N,4.3%).

Workup

  1. filtrationfiltered through Kieselghur
  2. customthe solvent removed by evaporation
  3. customthis was recrystallised from acetone-ether

Sources & evidence

ORD record
ord-e03f2db398654eb49c135beb30923a74
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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