Sodium Hydroxide → 2-{[(4-Fluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

HRID 2286223Notes

Reaction equation

HRID 2286223 reaction equation
[F: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:19]>C(O)C>[ClH:19].[F: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 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 677894-Fluorothiophenol

Product 1

HCID 127602222-{[(4-Fluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)Yield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Fluorobenzenethiol (5 g) was added to a solution of sodium hydroxide (3.14 g) in ethanol (50 ml) and the resulting solution was treated with 2-picolyl chloride, hydrochloride (6.4 g) in ethanol (25 ml) and the mixture was stirred for 6 hours at ambient temperature. The mixture was filtered, the solvent removed by evaporation and the residue was converted into the hydrochloride with ethereal HCl. Recrystallisation from ethanol-ether gave 2-(((4-fluorophenyl)thio)methyl)pyridine, hydrochloride (7 g) mp 190°-2° C. (Found: C,56.1; H, 4.4; N,5.2 C12H10FNS.HCl requires C,56.4; H,4.3; N,5.4%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed by evaporation
  3. customRecrystallisation from ethanol-ether

Sources & evidence

ORD record
ord-08becd3f711847f284a872e6929a01b4
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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