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

HRID 2219243Notes

Reaction equation

HRID 2219243 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-bc4b6602f4764214a89a441b8998c349
Source dataset
uspto-grants-2008_08
Patent number
US07414066B2

Reaction notes

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