Dimethyl Sulfoxide → HCID 53956337, compound

HRID 2303432Notes

Reaction equation

HRID 2303432 reaction equation
[Cl:1][C:2]1[C:3]([CH2:9][CH2:10][O:11][CH2:12][CH3:13])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:14][S:15](C)=O>[Cl-].[Na+].O>[Cl:1][C:2]1[C:3]([CH2:9][CH2:10][O:11][CH2:12][CH3:13])=[N:4][C:5]([S:15][CH3:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 18461245HCID 18461245, compound

Product 1

HCID 53956337HCID 53956337, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

3,6-Dichloro-2-(2-ethoxyethyl)-pyridine (1.18 g, 5.00 mmol) was dissolved in 25 mL DMSO, treated with NaSCH3 (0.53 g, 7.5 mmol), and stirred at room temperature overnight. The mixture was diluted with brine, then extracted with, EtOAc. The combined EtOAc extracts were combined, dried over Na2SO4, and concentrated in vacuo to yield 3-chloro-2-(ethoxyethyl)-6-(methylthio)pyridine (0.91 g, 76%) as a yellow oil, used without further purification.

Workup

  1. additiontreated with NaSCH3 (0.53 g, 7.5 mmol)
  2. extractionextracted with, EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2756abc4cc584cffbac38293aed70068
Source dataset
uspto-grants-2002_08
Patent number
US06432990B1

Reaction notes

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