4-Methyl-N-(prop-2-yn-1-yl)benzenesulfonamide

Add triethylamine (9.5 mL, 70 mmol, 1.4 equivalents), followed by tosyl chloride (9.53 g) portionwise to a stirred solution of propargylamine (3.84 mL, 60 mmol) in dry dichloromethane (50 mL, 1.2 M) at 0°C under argon atmosphere. Stir the mixture overnight at room temperature. Add water (50 mL) to the mixture. Extract the aqueous layer by dichloromethane (2 × 50 mL). Dry the combined organic layers over MgSO4. Concentrate the combined organic layers under reduced pressure.

[1]Bodinier, Florent et al. Low-valent dialkoxytitanium(ii): a useful tool for the synthesis of functionalized seven-membered ring compounds†.”Chemical Communications 29 (2021): 3603–3606.