Acetone → 4-Methyl-N,N-diprop-2-yn-1-ylbenzenesulfonamide

HRID 2353446Notes

Reaction equation

HRID 2353446 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]#[CH:20].[CH3:22][C:23]([CH3:25])=O>CCOCC.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:25][C:23]#[CH:22])[CH2:18][C:19]#[CH:20])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyne

Product 1

HCID 3291474-Methyl-N,N-diprop-2-yn-1-ylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of p-toluenesulfonamide (2.55 g) in acetone (100 mL) were added potassium carbonate (4.44 g) and propargyl chloride (5 g) and the mixture was refluxed overnight. The mixture was cooled, diluted with ether and brine. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified on a Biotage Horizon® system (silica, ethyl acetate gradient 13-25% in hexane) to yield the title compound.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureThe mixture was cooled
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified on a Biotage Horizon® system (silica, ethyl acetate gradient 13-25% in hexane)

Sources & evidence

ORD record
ord-bcb37cc2fe0b4ee69ffaf8b8a8a05ba4
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

Loading…