Water → HCID 69020953, compound

Participants

Reaction Steps

A solution of 3-(4-bromo-phenyl)-2-(toluene-4-sulfonyl)-acrylonitrile (38.76 g, 0.107 mol, prepared directly above) in anhydrous THF (500 mL) is treated with DBU (65.00 mL, 0.434 mol), followed by ethyl isocyanoacetate (25.00 g, 0.214 mol). The resulting dark-brown reaction mixture is allowed to stir at room temperature for 3 hours. The reaction mixture is poured into water (1,000 mL) and extracted with EtOAc (3×250 mL each). The combined organics are washed with 1 N HCl (250 mL), water (250 mL), brine (250 mL), dried over anhydrous Na2SO4, filtered, then concentrated in vacuo to afford an off-white solid. The solid is dissolved in a minimum amount of EtOAc, then treated with excess hexanes, causing a solid to crash out. The solid is recovered by vacuum filtration, washed with hexanes, and dried under vacuum filtration to afford the title compound (23.90 g, 69.9% crude yield) as a off-white solid: 1H NMR (500 MHz; CDCl3) δ 1.22 (t, 3H), 4.26 (q, 2H), 7.39 (d, 2H), 7.45 (d, 1H), 7.55 (d, 2H), 9.70 (bs, 1H).

Provenance & Evidence