Dimethyl Sulfoxide → 4,N-Dihydroxy-benzamidine

Participants

Reaction Steps

To a dimethylsulfoxide (100 mL) solution of 10.0 g of 4-cyanophenol was dropwise added 12.9 mL of a 50% hydroxylamine aqueous solution at room temperature over a period of 6 minutes, which was then stirred at the same temperature for 14 hours. Chloroform, a 1 mol/L sodium hydroxide aqueous solution, and water were added to the reaction mixture. The aqueous layer was separated and washed sequentially with toluene, chloroform, and toluene, to which water was then added, followed by adjustment to pH 7.2 using 6 mol/L hydrochloric acid. After stirring this mixture at room temperature for 30 minutes, the precipitate was collected by filtration and washed with water to provide 8.88 g of N′, 4-dihydroxybenzamidine as white solid form.

Provenance & Evidence