Dimethyl Sulfoxide → HCID 53956337, compound

HRID 840659Notes

Reaction equation

HRID 840659 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-d1f27686beb741a281f47db82e05ddd1
Source dataset
uspto-grants-2002_04
Patent number
US06369083B1

Reaction notes

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