Methanol → 5-(Methylthio)-2-nitropyridine

HRID 1523265Notes

Reaction equation

HRID 1523265 reaction equation
CO.[S-2:3].[CH3:4][Na].Cl[C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[N:11][CH:12]=1>O>[CH3:4][S:3][C:7]1[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 2598065-Chloro-2-nitropyridineHCID 178477781HCID 178477781, compound

Product 1

HCID 220361825-(Methylthio)-2-nitropyridineYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The methanol solution (2000 mL) of methyl sodium sulfide (150 g) was added dropwise into the methanol solution (4000 mL) of 5-chloro-2-nitropyridine (300 g), and the reaction temperature was kept below 0° C. After completing the dropping, the reactant was heated to room temperature, and stirred overnight. The solvent of the reaction mixture was discarded and 5 liters of water was added into the residue, then extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. The yellow and solid target compound (270 g) was obtained by filtration and concentration under reduced pressure. 1H-NMR (300 MHz, CDCl3) δ 2.61 (3H, s), 7.73 (1H, dd), 8.18 (1H, d), 8.40 (1H, d). LC-MS m/z: 171 [M++1].

Workup

  1. customwas kept below 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated NaCl solution
  4. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-0597c99c327a4604af4fd7778cbc95d9
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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