Water → 6-(Methylthio)-3-pyridinecarboxaldehyde

HRID 1747531Notes

Reaction equation

HRID 1747531 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[CH3:10][S-:11].[Na+].O>CN(C=O)C>[CH3:10][S:11][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27640536-Chloropyridine-3-carbaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 450837916-(Methylthio)-3-pyridinecarboxaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (5.0 mL) was dissolved 6-chloronicotinaldehyde (300 mg, 2.12 mmol). Sodium thiomethoxide (178 mg, 2.54 mmol) was added and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 6-(methylthio)nicotinaldehyde (239 mg, 74%).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-bede641e31474cfdb4de9d5e028b3bb0
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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