Potassium Carbonate → N-(3-(2-chlorophenyl)allyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

HRID 2280071Notes

Reaction equation

HRID 2280071 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]#[CH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]>>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:24]=[CH:23][CH2:22][N:11]([CH2:12][C:13]#[CH:14])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 37127464-methyl-N-(prop-2-yn-1-yl)benzenesulfonamideHCID 11644319(E)-1-(3-Bromoprop-1-en-1-yl)-2-chlorobenzene

Product 1

HCID 86702677N-(3-(2-chlorophenyl)allyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamideYield 78.2%

Procedure

To an oven-dried, 100 mL, three-necked round-bottomed flask equipped with a stir bar, two septa and a nitrogen gas inlet adaptor, was added 4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide (1.0 g, 4.8 mmol) and K2CO3 (2.69 g, 19.2 mmol). The flask was evaporated and refilled with nitrogen three times, then MeCN (60 mL) was added. (E)-1-(3-bromoprop-1-en-1-yl)-2-chlorobenzene (1.66 g, 7.2 mmol) was added dropwise via syringe, turning the solution dark yellow. The mixture was heated at reflux and stirred overnight. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:9). At the end of the reaction the solvent was removed in vacuo. The reaction residue was taken up in saturated NaHCO3 solution (70 mL) and extracted with ether (3×50 mL). The combined organic layers were washed with brine (70 mL), dried over Na2SO4, gravity filtered and concentrated under reduced pressure. The reaction residue was purified by silica gel flash chromatography, eluting with AcOEt/n-hexane 1:9, to provide 1.35 g of the title compound as a light yellow solid in a 78% yield.

Workup

  1. customTo an oven-dried, 100 mL, three-necked round-bottomed flask equipped with a stir bar
  2. customThe flask was evaporated
  3. additionrefilled with nitrogen three times
  4. additionMeCN (60 mL) was added
  5. temperatureThe mixture was heated
  6. temperatureat reflux
  7. customThe consumption of the starting material
  8. customAt the end of the reaction the solvent
  9. customwas removed in vacuo
  10. extractionextracted with ether (3×50 mL)
  11. washThe combined organic layers were washed with brine (70 mL)
  12. dry with materialdried over Na2SO4, gravity
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe reaction residue was purified by silica gel flash chromatography
  16. washeluting with AcOEt/n-hexane 1:9

Sources & evidence

ORD record
ord-c48de358f29e4c98b42131a05b0e3a34
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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