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

HRID 627593

Reaction equation

HRID 627593 reaction equation
[CH3:1][S:2]([CH2:5][C:6]#N)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].I[CH3:15].C[N:17]([CH:19]=O)C>>[CH3:15][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[C:19]#[N:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrile

Product 1

HCID 3014848Propanenitrile, 2-methyl-2-(methylsulfonyl)-Yield 78%

Procedure

To a solution of 2-(methylsulfonyl)acetonitrile (60 g, 504 mmol) in DMF (252 mL) at 0° C. was added potassium carbonate (209 g, 1511 mmol) portion-wise, followed by iodomethane (136 mL, 1511 mmol). After 15 minutes, the ice bath was removed and the reaction was stirred at RT for 48 hours. The reaction mixture was filtered through a Celite pad, and the filter cake was rinsed with ethyl acetate and ether. The combined filtrates were concentrated and partitioned between ether and water. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the titled intermediate (58 g, 78% yield) as an off-white solid.

Workup

  1. customthe ice bath was removed
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. washthe filter cake was rinsed with ethyl acetate and ether
  4. concentrationThe combined filtrates were concentrated
  5. custompartitioned between ether and water
  6. dry with materialThe organic portion was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e10f9ea604e493a8d783fc1f5d52e00
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Linked notes

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