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

HRID 239906

Reaction equation

HRID 239906 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

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 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.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e00a7859e5e942a5988e009082c9e4a9
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Linked notes

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