Ammonium Chloride → Benzenecarboximidamide, N-hydroxy-3-iodo-

Participants

Reaction Conditions

Reaction Steps

3-Iodobenzonitrile (7.00 g, 30.6 mmol) was dissolved in ethanol (153 mL), and the mixture was stirred at 90° C. for 2 hours after adding hydroxylamine hydrochloride (4.30 g, 61.2 mmol) and N,N-diisopropylethylamine (10.5 mL, 61.2 mmol). After adding an aqueous ammonium chloride solution, insoluble were separated by filtration through sellite. The organic layer of the filtrate was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography to give N′-hydroxy-3-iodobenzamidine (8.37 g, quantitative).

Provenance & Evidence