Water → Propanenitrile, 2-methyl-2-(methylsulfonyl)-

Reaction equation

[CH3:1][S:2]([CH2:5][C:6]#N)(=[O:4])=[O:3].[CH3:8]I.[H-].[Na+].O.C[N:14]([CH3:17])C=O>>[CH3:8][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[C:17]#[N:14]

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 75283(Methylsulfonyl)acetonitrile

Product 1

HCID 3014848Propanenitrile, 2-methyl-2-(methylsulfonyl)-Yield 58%

Procedure

To a solution of methylsulfonylacetonitrile (25 g) and methyl iodide (27.4 mL) in N,N-dimethylformamide (300 mL) was added sodium hydride (20 g) at 0° C., and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (18 g, yield 58%) as colorless crystals.