Tetrahydrofuran → HCID 22066046, compound

Participants

Reaction Steps

This reaction was carried out in a 100 ml round bottom flask. N′-[(1E)-1-(1-acetylpiperidin-4-yl)-2-pyrimidin-4-ylethylidene]-4-methylbenzenesulfonohydrazide (7) (5g, 11 mmol) was charged to the reactor, followed by tetrahydrofuran (“THF”, 31 ml), which, in turn, was followed by 2.15 ml of triethylamine (“TEA”, 2.15 ml) and 4-dimethylaminopyridine (“DMAP”, 0.134 g). 4-Chlorobenzoyl chloride (8) (“4-CBC”, 2.09 ml) was then charged all at once while stirring the mixture. The reaction was brought to reflux. Liquid chromatography indicated that the reaction was complete in just over 1 hr. The solution was washed with saturated ammonium chloride (2×25 ml), and the THF was removed in vacuo to yield a yellow oil (11.18 g), which solidified upon sitting. Recrystallization from ethanol/water yielded 4.88 g of a white powder (76% yield). The product had the following characteristics: 1H NMR (CDCl3, 300 MHz) δ 9.20 (1H, s), 7.63 (2H, d, J=8.4 Hz), 7.45 (2H, d, J=8.4 Hz), 7.30 (2H, d, J=8.1 Hz), 7.29 (1H, s), 7.21 (2H, d, J=8.4 Hz), 6.64 (1H, d, J=5.1 Hz), 4.71–4.52 (1H, m), 4.01–3.82 (1H, m), 3.59–3.44 (1H, m), 3.28–3.08 (1H, m), 2.84–2.58 (1H, m), 2.46 (3H, s), 2.16 (3H, s), 2.02–1.62 (4H, m). 13C NMR (CDCl3, 75 MHz) δ 169.11, 158.91, 146.39, 136.80, 134.55, 132.01, 130.13, 129.19, 126.72, 34.91, 31.15, 22.01, 21.69.

Provenance & Evidence