Hydrochloric Acid → HCID 86718990, compound

Participants

Reaction Conditions

Reaction Steps

To ethyl 2-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenylcarbamoyl)-hydrazinecarboxylate (1.31 g, 3.59 mmol) in methanol (17.93 mL) was added K2CO3 (1.239 g, 8.96 mmol). The mixture was stirred at 55° C. for 30 minutes. After cooling to room temperature, 4N HCl in dioxane (3.59 mL, 14.34 mmol) was added. The precipitate was filtered, and the filtrate was concentrated in vacuo. The residue was then purified by silica gel chromatography (40-100% ethyl acetate/heptane) giving 4-(4-(2-(2-(prop-2-ynyloxy)ethoxy)ethoxy)phenyl)-1,2,4-triazolidine-3,5-dione (I-7d: 318 mg, 28%) as a white oily solid. LC-MS (M+1) 320.0, t=0.73 minute. 1H NMR (400 MHz, CDCl3) δ ppm 2.48 (t, J=2.15 Hz, 1 H) 3.68-3.83 (m, 4 H) 3.83-3.97 (m, 2 H) 4.11-4.32 (m, 4 H) 7.04 (d, J=8.84 Hz, 2 H) 7.36 (d, J=8.84 Hz, 2 H).

Provenance & Evidence