Water → N-(3-Oxo-3-phenylpropyl)methanesulfonamide

HRID 604575Notes

Reaction equation

HRID 604575 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].Cl[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].O>CN(C)C=O>[CH3:1][S:2]([NH:5][CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 702953-ChloropropiophenoneHCID 72879Methanesulfonamide

Product 1

HCID 57423897N-(3-Oxo-3-phenylpropyl)methanesulfonamideYield 21.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonamide (0.476 g, 5.00 mmol) was dissolved in N,N-dimethyl-formamide (DMF, 10 mL), and 60% sodium hydride (0.275 g, 5.00 mmol) was added at 0° C., then the mixture was stirred at the same temperature for 20 minutes. Subsequently, to the mixture was added 3-chloropropiophenone (843 mg, 5.00 mol), and the mixture was stirred at the same temperature for 2 hours, and then further stirred at room temperature for 15 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=20/1) to give N-methanesulfonyl-3-aminopropiophenone (240 mg, 21%).

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. stirringfurther stirred at room temperature for 15 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-0ca34d6cf74d4f5e8573cb62c8b8fd5d
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

Loading…