22059-22-9

75-05-8

22059-22-9

The general procedure for the synthesis of N'-hydroxyacetamidine from acetonitrile is as follows:(a) Preparation of N-hydroxyacetamidine amide: Phenolphthalein (0.05 g) was added to a solution of hydroxylamine hydrochloride (35 g, 0.5 mol) in ethanol (200 ml) as an indicator. Sodium ethanol solution (324 ml, 21% v/v) was added slowly over a period of 1 hour. After 3 hours of reaction, acetonitrile (13.8 g) was added and the reaction was stirred at room temperature for 2 hours followed by heating at 40°C for 48 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered and the solvent was removed under reduced pressure. The residue was allowed to stand at room temperature for 48 h. Methanol (1 liter) was then added to dissolve the crude product and it was adsorbed onto silica. Purification by silica column chromatography using 9:1 dichloromethane:methanol as eluent gave the target product N'-hydroxyacetamidine (20.33 g, 81% yield). The product was characterized by 1H NMR (d6-DMSO): δ = 1.60 (3H, s), 5.33 (2H, br), 8.65 (1H, s).