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

HRID 1649134Notes

Reaction equation

HRID 1649134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[OH-].[Na+].Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][Cl:20]>C(O)C>[ClH:20].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 23642Thioguaiacol

Product 1

HCID 129532922-{[(2-Methoxyphenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)Yield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Methoxybenzenethiol (5 g) was added to a solution of sodium hydroxide (2.85 g) in ethanol (50 ml) and the resulting mixture was treated with 2-picolyl chloride, hydrochloride (5.7 g) in ethanol (25 ml) at 0° C. After 16 hours at ambient temperature the mixture was filtered through kieselghur and evaporated. The residue was converted into the hydrochloride in ether with ethereal HCl solution and this was recrystallised from propan-2-ol/acetone to give 2-(((2-methoxyphenyl)thio)methyl)pyridine, hydrochloride (4.0 g) mp 141°-3° C. (Found: C,58.5; H,5.4; N,4.9 C13H13NOS.HCl requires C,58.3; H,5.3; N,5.2%).

Workup

  1. filtrationAfter 16 hours at ambient temperature the mixture was filtered through kieselghur
  2. customevaporated
  3. customthis was recrystallised from propan-2-ol/acetone

Sources & evidence

ORD record
ord-5993ef00736e433dad18df4a966582cd
Source dataset
uspto-grants-1983_11
Patent number
US04415579

Reaction notes

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