Water → N'-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide

Participants

Reaction Conditions

Reaction Steps

4-Amino-N′-hydroxy-N-(2-methoxyethyl)-1,2,5-oxadiazole-3-carboximidamide (248.0 g, 1.23 mol) was mixed with water (1 L). Potassium hydroxide (210 g, 3.7 mol) was added. The reaction was refluxed at 100° C. overnight (15 hours). TLC with 50% ethyl acetate (containing 1% ammonium hydroxide) in hexane indicated reaction completed (product Rf=0.6, starting material Rf=0.5). LCMS also indicated reaction completion. The reaction was cooled to room temperature and extracted with ethyl acetate (3×1 L). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (201 g, 81%) as a crude off-white solid. LCMS for C6H12N5O3 (M+H)+: m/z=202.3 1H NMR (400 MHz, DMSO-d6): δ 10.54 (s, 1 H), 6.22 (s, 2 H), 6.15 (t, J=5.8 Hz, 1 H), 3.45 (t, J=5.3 Hz, 2 H), 3.35 (m, 2 H), 3.22 (s, 3 H).

Provenance & Evidence