Methyl iodide → HCID 68276426, compound

HRID 1487362Notes

Reaction equation

HRID 1487362 reaction equation
[CH3:1]I.[OH:3][C:4]1[C:11]([I:12])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([S:13][CH3:14])[N:5]=1>O1CCOCC1.C(=O)([O-])[O-].[Ag+2]>[I:12][C:11]1[C:4]([O:3][CH3:1])=[N:5][C:6]([S:13][CH3:14])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178503563HCID 178503563, compound

Product 1

HCID 68276426HCID 68276426, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

905 μl (2 eq) of methyl iodide and 2.1 g (1.05 eq) of silver carbonate are added successively to a solution of 2.12 g (7.26 mmol) of 6-hydroxy-5-iodo-2-(methylthio)nicotinonitrile in 20 ml of 1,4-dioxane. The reaction medium is stirred at 60° C. for 5 hours. The solid is filtered and the residue rinsed thoroughly with methanol. The filtrate is evaporated and the residue purified by silica column chromatography (4:6 dichloromethane/cyclohexane as eluent) to yield 1.52 g (68%) of 5-iodo-6-methoxy-2-(methylthio)nicotinonitrile in the form of a white powder.

Workup

  1. filtrationThe solid is filtered
  2. washthe residue rinsed thoroughly with methanol
  3. customThe filtrate is evaporated
  4. customthe residue purified by silica column chromatography (4:6 dichloromethane/cyclohexane as eluent)

Sources & evidence

ORD record
ord-e6bfc883de2847b1b096a3f5a3b9b4a7
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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