Methanesulfonyl chloride → N-(2-oxo-2-phenylethyl)methanesulfonamide

HRID 1822061Notes

Reaction equation

HRID 1822061 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>CN(C=O)C>[O:5]=[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:2][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 21893541N-(2-oxo-2-phenylethyl)methanesulfonamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-1-phenylethanonehydrochloride (1a) (1715 mg, 10 mmol) in DMF (20 mL) was added TEA (2.8 mL, 20 mmol). Upon cooling under ice-water bath, methylsulfonyl chloride (0.77 mL, 10 mmol) was added slowly and the reaction mixture stirred at RT for 12 h. The mixture was partitioned between dichloromethane and brine, dried over sodium sulfate and then concentrated in vacuo to give the title compound (2100 mg, 98%) as an off white solid. MS APCI, m/z=214 (M+1). LCMS: 1.19 min.

Workup

  1. temperatureUpon cooling under ice-water bath
  2. customThe mixture was partitioned between dichloromethane and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1ca54da4036490c96bf4f54fdfc20cd
Source dataset
uspto-grants-2009_10
Patent number
US07608628B2

Reaction notes

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