4-Toluenesulfonyl chloride → p-Toluenesulfonamide, N-(2-dimethylaminoethyl)-

HRID 1835866Notes

Reaction equation

HRID 1835866 reaction equation
C[NH:2][CH2:3][CH2:4][NH:5][CH3:6].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH2:18]1COCC1>>[CH3:18][N:5]([CH3:6])[CH2:4][CH2:3][NH:2][S:7]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8070N,N'-Dimethylethylenediamine

Product 1

HCID 101480p-Toluenesulfonamide, N-(2-dimethylaminoethyl)-Yield 93%

Procedure

To 10.5 g of N,N′-dimethylethylenediamine in 250 ml of THF was added 26 g of tosylchloride (TsCl) in small portions at room temperature. After 16 hours, solvents were evaporated and the residue was apportioned between H2O and CH2Cl2. A CH2C2 layer was separated and washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. About 26.5 g of N,N-dimethyl-N′-tosylethylenediamine (93%) was produced. The reaction steps are shown below:

Workup

  1. customsolvents were evaporated
  2. customA CH2C2 layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-22dd9bb79b8549f6b2005cb8f60b3e3f
Source dataset
uspto-grants-2004_08
Patent number
US06774082B2

Reaction notes

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