Ethanol → 2-[1-(5-Cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester

Participants

Reaction Steps

2-(5-cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester (1.62 g, 6.2 mmol) and p-toluenesulfonhydrazide (2.31 g, 12.4 mmol) were refluxed in 50 mL ethanol for 36 h. The reaction was concentrated in vacuo, then purified by flash chromatography on silica gel using ethyl acetate/hexane (0-25%) as the eluent to give 2-[1-(5-cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester (1.77 g, 66%) as a mixture of cis and trans isomers. 1H NMR (500 MHz, CDCl3) 7.87 (1H, d, J=8.24 Hz), 7.78 (0.5H, m), 7.76 (1H, d, J=8.24 Hz), 7.65 (0.5H, m), 7.61 (0.5H, dd, J 2.14, 6.71 Hz), 7.44 (0.5H, dd, J=2.14, 5.80 Hz), 7.36 (2H, dd, J=3.96, 7.93 Hz), 7.31 (0.5H, t, J=8.54 Hz), 7.18 (0.5H, t, J=8.54 Hz), 4.22 (1H, m), 4.12 (2H, dq, J=7.32, 4.27 Hz), 2.46 (3H, 2s), 2.20 (0.5H, m), 1.99 (0.5H, m), 1.66 (0.5H, mn), 1.43 (0.5H, m), 1.31 (2H, m), 1.27 (3H, dt, J=7.02, 3.67 Hz). MS m/e 430.13 (M+H)+.

Provenance & Evidence