Potassium Carbonate → HCID 86718996, compound

Participants

Reaction Conditions

Reaction Steps

To ethyl 2-(2,3-bis(prop-2-ynyloxy)propylcarbamoyl)hydrazinecarboxylate (I-13c: 855 mg, 2.88 mmol) in EtOH (14.400 mL) was added potassium carbonate (1590 mg, 11.50 mmol). The mixture was stirred at 65° C. for 16 h. After cooling to room temperature, the mixture was concentrated. HCl 1N was added up to pH-3, and then extracted with AcOEt twice, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (30-100% AcOEt/heptane), and then repurified by silica gel chromatography (0-20% MeOH/CH2Cl2), giving 4-(2,3-bis(prop-2-ynyloxy)propyl)-1,2,4-triazolidine-3,5-dione (1-13d: 238 mg, 33%) as a colorless oil. LC-MS (M+1) 252.1, t=0.72 minute. 1H NMR (400 MHz, CD3CN) δ ppm 2.69 (t, J=2.27 Hz, 1 H) 2.76 (t, J=2.27 Hz, 1 H) 3.47-3.69 (m, 4 H) 3.93-4.04 (m, 1 H) 4.20 (d, J=2.27 Hz, 2 H) 4.22-4.28 (m, 2 H).

Provenance & Evidence