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

HRID 1156766Notes

Reaction equation

HRID 1156766 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-9cada3259ab64d1caac33195679a790d
Source dataset
uspto-grants-1982_06
Patent number
US04337259

Reaction notes

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