Dimethyl Sulfoxide → N-Hydroxy-4-iodo-benzamidine

Participants

Reaction Steps

17.3 g (249 mmol) of hydroxylamine hydrochloride and then 35 ml (251 mmol) of triethylamine are added to 80 ml of DMSO. A voluminous white precipitate forms, and the reaction mixture is diluted with a small amount of THF. After stirring for 1 hour, the precipitate is filtered off. The filtrate is collected and then transferred to a flask to which there are added 9.55 g (41.7 mmol) of 4-iodobenzonitrile. The reaction mixture is stirred overnight at ambient temperature and is then cooled in an ice bath and 200 mL of water are added. The precipitate is filtered off to yield the expected product.

Provenance & Evidence