Methyl iodide → HCID 18759792, compound

HRID 1634014Notes

Reaction equation

HRID 1634014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH:13]=[CH:12][N-:11][C:10]2=[S:14])=[CH:4][N:3]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:13][CH2:12][N:11]=[C:10]2[S:14][CH3:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178527850HCID 178527850, compound

Product 1

HCID 18759792HCID 18759792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.6 g of 3-(2-chloropyrid-5-yl-methyl)-pyrrolide-2-thione are added to a mixture of 0.1 g of sodium hydride (50% in oil) and 10 ml of dimethylformamide. The mixture is stirred for 20 minutes at room temperature and then 0.38 g of methyl iodide is added. The reaction mixture is stirred for a further 30 minutes at room temperature, poured onto ice-water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated to dryness by evaporation in vacuo. The title compound is obtained in the form of an oil (compound 3.2).

Workup

  1. stirringThe reaction mixture is stirred for a further 30 minutes at room temperature
  2. additionpoured onto ice-water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness by evaporation in vacuo

Sources & evidence

ORD record
ord-694902be3b874594954a1b3f92316568
Source dataset
uspto-grants-2003_01
Patent number
US06506743B2

Reaction notes

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