Methanol → 5-(Methylthio)-2-nitropyridine

HRID 746651Notes

Reaction equation

HRID 746651 reaction equation
CO.Cl[C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[N:8][CH:9]=1.[CH3:13][S-:14].[Na+]>O>[CH3:13][S:14][C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 2598065-Chloro-2-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 220361825-(Methylthio)-2-nitropyridineYield 45.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol (40 mml) solution of 5-chloro-2-nitropyridine (2.0 g. 12.6 mmol) was added dropwise to a methanol (20 ml) solution of sodium thiomethoxide (1.02 g, 13.9 mmol) while being cooled with ice, and after the mixture was stirred for 13 hours while raising its temperature to the room temperature, water added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the resulting crude product was recrystalized with ethyl acetate-hexane to obtain 972 mg (yield 45%) of 5-methylthio-2-nitropyridine.

Workup

  1. temperaturewhile being cooled with ice
  2. additionadded to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  6. distillationThereafter, the solvent was distilled off
  7. customthe resulting crude product was recrystalized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-41afd04ecdd04bf3a0c5a3343c11ceff
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

Loading…