Oxalic Acid → HCID 68557137, compound

Participants

Reaction Steps

To a solution of 3-(3,3-dimethyl-2-oxo-butyl)-3H-1,3,4-oxadiazol-2-one (0.91 g, 4.59 mmol) in a mixture of 2-propanol (4 mL) and water (0.11 mL) is added hydrazine monohydrate (0.34 mL, 6.89 mmol). The reaction mixture is heated to reflux under nitrogen for 5 h, then a solution of oxalic acid (0.13 g, 1.38 mmol) in 2-propanol (5 mL) is added to the hot solution. The resulting precipitate is removed hot by filtration. The filtrate is concentrated in vacuo and the residue is purified on a pad of silica gel, eluting with heptane:EtOAc gradient to afford N-(6-tert-butyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-acetamide (0.546 g, 56%) as a solid. MS: 213 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 8.29 (s, 1H), 7.64 (s, 1H), 4.22 (s, 2H), 2.04 (s, 3H), 1.15 (s, 9H).

Provenance & Evidence