1-Butyne → 2-(But-1-yn-1-yl)-benzenesulfonamide

Participants

Reaction Steps

0.1 g of bis(triphenylphosphine)palladium(II) chloride, 0.05 g of copper iodide and 18.5 ml of triethylamine are added to a solution of 5 g of 2-iodobenzenesulfonamide in 70 ml of N,N-dimethylformamide. At room temperature, argon and 1-butyne are slowly introduced. After 18 hours the thin-layer chromatogram no longer shows any 2-iodobenzenesulfonamide. The dimethylformamide is evaporated off at 0.1 torr and 40°, and the residue is chromatographed on 300 g of silica gel (Merck ST 60, 40-63 μm). Methylene chloride is used as eluant. In that manner, after concentration of the product-containing fractions at 15 torr and 40°, white pulverulent 2-(but-1-yn-1-yl)-benzenesulfonamide is obtained: 1H-NMR (300 MHz, CDCl3): 8.0 (d, d, 1H); 7.35 (d, d, 1H); 7.29 (d, t, 1H); 7.23 (d, t, 1H); 5.13 (s, 2H); 2.32 (q, 2H); 1.18 (t, 3H).

Provenance & Evidence