Hydrochloric Acid → HCID 87545492, compound

Participants

Reaction Steps

tert-butyl [4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)-2-oxobutyl]methylcarbamate (50 mg, 0.112 mmol), hydroxylamine hydrochloride (50 mg, 0.720 mmol), and pyridine (1.5 mL) were stirred in ethyl alcohol (3 mL) in a sealed vial at 70° C., for 3 hr. The reaction was allowed to cool to room temperature and transferred to a separatory funnel with dichloromethane and washed with a saturation aqueous solution of sodium bicarbonate, brine, dried (MgSO4), filtered and the solvent removed, in vacuo, to give a clear oil. This material was adsorbed onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane to afford a white solid. This material was dissolved in diethyl ether and methanol and 4N HCl in dioxane was added a precipitate formed. The mixture was filtered to afford 0.028 g (62% Yield) of (2Z)-4-(2,2-dioxido-3-phenyl-2,1,3-benzothiadiazol-1(3H)-yl)-1-(methylamino)butan-2-one oxime as an off white solid.

Provenance & Evidence