Reaction Steps
To a solution of 3-[4-chloro-2-(toluene-4-sulfonylamino)-phenyl]-acrylic acid ethyl ester (3.00 g, 7.90 mmol) in NN-dimethylacetamide (15.0 ml) was added potassium carbonate (2.18 g, 15.8 mmol) and 2-bromo-4′-chloroacetophenone (2.03 g, 8.69 mmol). The reaction was stirred for 30 minutes, poured into 1N hydrochloric acid (30 ml) and extracted with methyl f-butyl ether (2×30 ml). The organic extracts were dried over magnesium sulfate, filtered, concentrated to a low volume. Hexanes was added and a solid precipitated. The precipitate was filtered to provide 3-{4-chloro-2-[[2-(4-chloro-phenyl)-2-oxo-ethyl]-(toluene-4-sulfonyl)-amino]-phenyl}-acrylic acid ethyl ester (3.19 g, 76%). mp=162-165° C. 1H NMR (300 MHz, CDCl3) d 1.38 (t, 3, J=7.2), 2.47 (s, 3), 4.28 (q, 2, J=7.2), 5.00 (bs, 2), 6.23 (d, 1, J=16.0), 7.29-7.36 (m, 4), 7.47 (d, 2, J=8.7), 7.54 (d, 1, J=8.4), 7.59 (d, 2, J=8.3), 7.74 (d, 1, J=16.0), 7.88 (d, 2, J=8.7). 13C NMR (75 MHz, CDCl3) d 14.33, 21.62, 57.72, 60.66, 112.49, 120.69, 128.07, 129.21, 129.58, 129.70, 131.22, 132.80, 133.83, 134.80, 135.84, 138.55, 139.28, 140.38, 144.46, 166.02, 191.70. IR 1720, 1698, 1590, 1338, 1313, 1179, 1161, 1089 cm−1. Analysis calculated for C26H23Cl2NO5S: C, 58.65; H, 4.35; N, 2.63. Found: C, 58.74; H, 4.56; N, 2.72.
