Dimethylamine → C-(4-methanesulfonyl-phenyl)-N,N-dimethyl-methanesulfonamide

HRID 896666Notes

Reaction equation

HRID 896666 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12](Cl)(=[O:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:16][NH:17][CH3:18]>C(Cl)Cl.[Cl-].[NH4+].C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([N:17]([CH3:18])[CH3:16])(=[O:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 674DimethylamineHCID 219624184-(Methylsulfonyl)benzenemethanesulfonyl chloride

Product 1

HCID 22350067C-(4-methanesulfonyl-phenyl)-N,N-dimethyl-methanesulfonamide

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (4-methanesulfonyl-phenyl)-methanesulfonyl chloride from Step 2 (1.0 g, 3.7 mmol) in CH2Cl2 (40 mL) was added dimethylamine (0.42 g, 9.3 mmol) dropwise. After 18 h, the resulting reaction mixture was diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (HCl 10%, NaHCO3, brine), dried (MgSO4), filtered, and concentrated to provided the C-(4-methanesulfonyl-phenyl)-N,N-dimethyl-methanesulfonamide compound.

Workup

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (HCl 10%, NaHCO3, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53b37fcf36f64c638d023624da51a376
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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