Water → methyl 6-(methylthio)nicotinate

HRID 1690144Notes

Reaction equation

HRID 1690144 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][S-:13].[Na+].O>CN(C=O)C>[CH3:12][S:13][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 4378561Sodium methanethiolate

Product 1

HCID 901959methyl 6-(methylthio)nicotinateYield 112.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-chloronicotinate (100 mg, 0.583 mmol) in N,N′-dimethylformamide (1.5 mL) was added with sodium thiomethoxide (41 mg) under ice-cold conditions, and then stirred at room temperature for 3 hours. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and methyl 6-(methylthio)nicotinate (120 mg, yield >100%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-97fd91fdb31c464d8ab0679e533cb5c0
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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