Hydrochloric Acid → HCID 501143, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred room temperature solution of 3.0 g (0.01 mole) of 2-[[1-(5-acetylamino-2-methylphenyl)ethyl]thio]-pyridine-N-oxide in 10 ml of methanol were added 0.12 g of Na2WO4 followed by 1 g of 35% hydrogen peroxide added over 20 minutes. The exothermic reaction was cooled using a room temperature water bath. The mixture was stirred for 20 minutes, and then treated dropwise with another 1.3 g of 35% H2O2. The mixture was warmed to 35-43° C. for two hours, and then left to stir at room temperature overnight. The mixture was then treated with 5 ml of ethanol, 10 ml of water, and 5 ml of concentrated HCl and heated on a steam cone for one hour. The mixture was cooled, diluted with 20 ml of water and filtered to remove a solid. The filtrate was made basic with concentrated aqueous ammonium hydroxide to give a tacky solid. This solid was taken up in 30 ml of water and 3 ml of concentrated HCl and some insoluble material was filtered off. The filtrate was basified to give a solid precipitate that was filtered off, washed with water, and left to dry overnight. The dry solid weighed 0.85 g and melted at 165-170° C. Recrystallization gave a solid with a melting point of 184-188° C. and having infrared and NMR spectra consistent with the proposed structure.

Provenance & Evidence