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

To an oven-dried, 100 mL three-necked round-bottomed flask equipped with a stir bar, two septa and a nitrogen inlet adaptor was added 4-methyl-N-(prop-2-yn-1-yl) benzenesulfonamide (S17) (1.0 g, 4.8 mmol) and potassium carbonate (2.69 g, 19.2 mmol). The flask was evacuated and refilled with nitrogen three times, then MeCN (60 mL) was added. (E)-1-(3-Bromoprop-1-en-1-yl)-2-chlorobenzene (S14) (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). The solvent was removed in vacuo, and the reaction residue was taken up in sat'd 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.

1. customTo an oven-dried, 100 mL three-necked round-bottomed flask equipped with a stir bar
2. customThe flask was evacuated
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. customThe solvent was removed in vacuo
9. extractionextracted with ether (3×50 mL)
10. washThe combined organic layers were washed with brine (70 mL)
11. dry with materialdried over Na2SO4, gravity
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe reaction residue was purified by silica gel flash chromatography
15. washeluting with AcOEt/n-hexane 1:9

ORD record

ord-4aed34963c044e89bffe9c7cd704fbc1

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133234B2