Water → N,2-Dimethyl-2-(methylsulfonyl)propanamide

HRID 623755Notes

Reaction equation

HRID 623755 reaction equation
[Na+].[CH3:2][S:3]([O-:5])=[O:4].N1C=CC=CC=1.Br[C:13]([CH3:19])([CH3:18])[C:14]([NH:16][CH3:17])=[O:15].O>CN(C=O)C.CCOC(C)=O>[CH3:17][NH:16][C:14](=[O:15])[C:13]([CH3:19])([S:3]([CH3:2])(=[O:5])=[O:4])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 2875602-Bromo-N,2-dimethylpropanamideHCID 2733271Sodium methanesulfinate

Product 1

HCID 64088538N,2-Dimethyl-2-(methylsulfonyl)propanamideYield 24.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of methanesulfinic acid sodium salt (310 mg, 3.04 mmol) in dry DMF (3.5 mL) was added under a nitrogen atmosphere, dry pyridine (0.5 mL) and 2-bromo-N,2-dimethylpropanamide (365 mg, 2.027 mmol). The reaction mixture was stirred at 50° C. overnight, cooled and H2O (5 mL) and EtOAc (10 mL) were added. The aqueous layer was separated and extracted twice with EtOAc (5 mL). The combined organic phase was washed with brine (20 mL) and dried over Na2SO4. The solution was concentrated in vacuo and stirred in heptane (25 mL). The solids were filtered to give the desired product (88 mg, 23%) as a white solid.

Workup

  1. additionwas added under a nitrogen atmosphere
  2. temperaturecooled
  3. customThe aqueous layer was separated
  4. extractionextracted twice with EtOAc (5 mL)
  5. washThe combined organic phase was washed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationThe solution was concentrated in vacuo
  8. stirringstirred in heptane (25 mL)
  9. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-39aaaab7e55d4c47bf0891f9cdd78753
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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