Methyl iodide → 2-(Methylthio)-5-nitropyridine

HRID 1860593Notes

Reaction equation

HRID 1860593 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.O.[C:12](=O)([O-])[O-].[Na+].[Na+].CI>O.C(O)C>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([S:1][CH3:12])=[CH:7][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2735133Sodium Carbonate MonohydrateHCID 178526723C5H4N2O2S

Product 1

HCID 44393132-(Methylthio)-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2-Mercapto-5-nitro pyridine (20.0 g, 128 mmol) was suspended in water/ethanol (43 mL/13 mL). Sodium carbonate monohydrate (17.49 g, 141 mmol, dissolved in 86 mL of water) was added to the above slurry dropwise. Methyl iodide (20.0 g, 141 mmol) was added to the above mixture and the mixture was stirred at room temperature for one hour. The solid was filtered and washed with water and ethanol to provide the title compound in quantitative yield.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water and ethanol

Sources & evidence

ORD record
ord-fe4a31190e49434187e19698dbb5e0c2
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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