Acetamide oxime

White crystals

(a) To a solution of 0.57 g (14.2 mmol, 1 eq) of NaOH in 5 ml of water, 1.00 g (14.2 mmol, 1 eq) of hydroxylamine was added. 15 mL of acetonitrile were added dropwise, the mixture wasstirred at room temperature overnight. Acetonitril and water were removed under vacuum and ethanol was added to the crude product. The product was filtered off and washed with ethanol giving 600 mg of the expected product (60percent).1H NMR 400MHz (CDCI)i 1.86 (s, 3H)To a solution of hydroxylamine (2.21 g, 67 MMOL) in water (5 mL) was added acetonitrile (3.5 mL, 2.75 g, 67 MMOL). Ethanol was added dropwise until a clear solution resulted. The mixture was cooled to 0°C, and sodium ethoxide (21.7 g of a 21percent solution in ethanol, 67 MMOL) was added. After completion of the addition, the reaction mixture was warmed to 35°C and stirred at that temperature for 3 days. The reaction mixture was then cooled to rt, and the solid residue (NaCI) was removed by filtration and washed with acetonitrile. The filtrate and the washings were combined, the solvents partially evaporated in vacuo, and conc HCI was added until the pH was-1. 0. The solvents were then evaporated until a yellow residue appeared. This residue was dissolved in hot ETOH and reprecipitated by adding diethylether. Needle-like crystals appeared from the solution which were filtered off. The filtrate was saved and kept in the freezer for several days to get a second crop. The product was obtained as colorless crystals (1.12 g, 15percent).APOS;H NMR (400 MHz, DMSO-d6). 6 2.09 (S, 3H), 8.45 (br, s, 1H), 10.64-10. 90 (br, 1H), 12.2-12. 5 (br, 1H).Acetonitrile (40.0 mL) and 50percent hydroxylammne in water (4.20 mL) were heated at reflux at 90°C for 24 h. The reaction mixture was cooled to 0°C and filtered. The residue was dried to give (7)- N-hydroxyethanimidamide (2.1 g, >100percent) as a white crystalline solid.LCMS (Method H): m/z 74 (M+H) (ES*), at 1.86 mm, UV inactive

Molecular Weight:74.08
XLogP3:-0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:74.048012819
Monoisotopic Mass:74.048012819
Topological Polar Surface Area:58.6
Heavy Atom Count:5
Complexity:49.6
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes