2-Chloro-6-methoxy-3-nitropyridine → 6-Methoxy-2-(methylthio)-3-nitropyridine

HRID 22885Notes

Reaction equation

HRID 22885 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH3:13][S-:14].[Na+]>CO>[CH3:12][O:11][C:4]1[N:3]=[C:2]([S:14][CH3:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 4378561Sodium methanethiolate

Product 1

HCID 225921666-Methoxy-2-(methylthio)-3-nitropyridineYield 60.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol (100 ml) solution of 2-chloro-6-methoxy-3-nitropyridine (2.0 g, 10.4 mmol) was added dropwise to a methanol (20 ml) solution of sodium thiomethoxide (805 mg, 10.9 mmol) while being cooled with ice, and the temperature thereof was raised to the room temperature and the mixed solution was stirred for 17 hours and the precipitated crystal was filtered to obtain 1.26 g (yield 59%) of 6-methoxy-2-methylthio-3-nitropyridine as a yellow powdery crystal.

Workup

  1. temperaturewhile being cooled with ice
  2. filtrationthe precipitated crystal was filtered

Sources & evidence

ORD record
ord-6934e36a66bd4d2ab69805f082bfda7e
Source dataset
uspto-grants-2005_02
Patent number
US06849647B1

Reaction notes

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