Methanol → Pyridine, 2-(methylthio)-3-nitro-

HRID 22881Notes

Reaction equation

HRID 22881 reaction equation
CO.Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:13][S-:14].[Na+]>O>[CH3:13][S:14][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 796132-Chloro-3-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 572042Pyridine, 2-(methylthio)-3-nitro-Yield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol (50 ml) solution of 2-chloro-3-nitropyridine (4.30 g, 27.1 mmol) was added dropwise to a methanol (30 ml) solution of sodium thiomethoxide (2.10 g, 28.5 mmol) while being cooled with ice, and the mixed solution was stirred for 17 hours. Water was then added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crystals were recrystallized from a mixture of an ethyl acetate-hexane mixture to obtain 2.93 g (yield 64%) of 2-methylthio-3-nitropyridine as a yellow needle crystal.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. distillationSubsequently, the solvent was distilled off
  6. customthe resulting crystals were recrystallized from a mixture of an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-7257ee8926b142a19f5f9af085d27b45
Source dataset
uspto-grants-2005_02
Patent number
US06849647B1

Reaction notes

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