Water → HCID 86693520, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-{2-[2-(but-3-yn-1-yloxy)-5-iodophenyl]hydrazin-1-ylidene}-2-chloroacetate (3.9 g, 9.27 mmol) in toluene (800 ml) was added triethylamine (13 ml, 9.32 mmol) and the mixture was then stirred under reflux (heating block at 125° C.) for 18 hours. After cooling to ambient temperature water (100 ml) and ethyl acetate (100 ml) were added and the mixture was transferred into a separation flask. The organic layer was separated, washed with brine (200 ml), dried over MgSO4, filtered and pre-absorbed onto a small amount of silica. Purification by FCC (silica, 0-20% ethyl acetate in heptane) provided 2.63 g (74%) of the title compound as crystalline solid. 1H NMR (500 MHz, CDCl3) δ ppm 1.43 (3H, t, J=7.17 Hz), 3.09 (2H, t, J=6.03 Hz), 4.45 (2H, q, J=7.17 Hz), 4.53 (2H, t, J=6.10 Hz), 6.81 (1H, s), 6.93 (1H, d, J=8.54 Hz), 7.61 (1H, dd, J=8.54, 2.14 Hz), 8.28 (1H, d, J=2.14 Hz);); M+1=385

Provenance & Evidence