Hydrochloric Acid → HCID 23532950, compound

Participants

Reaction Conditions

Reaction Steps

4.73 g (0.017 mol) of the title compound of Step E and 2.08 g (0.025 mol) of sodium acetate were added to 85 mL of methanol. The solution was cooled to about 0° C., and a solution of 17.66 g (0.029 mol) of OXONE® (purchased from Aldrich Chemical Company) in 85 mL of water was added dropwise while keeping the temperature below 6° C. The mixture was warmed to room temperature and stirred under nitrogen overnight. The mixture was diluted with 50 mL of water, cooled to about 0° C., acidified to around pH 2 with concentrated hydrochloric acid, and then extracted with chloroform (3×150 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to dryness. The residue was triturated in diethyl ether:hexane (1:9) which was decanted to yield 4.18 g of the title compound of Step F as a solid melting at 185° C. (dec). 1H NMR (Me2SO-d6): δ2.35 (s,3H), 2.5 (m,2H), 2.6 (s,3H), 3.5 (m,2H), 4.16 (m,2H), 4.2 (m,2H), 7.6 (s,1H).

Provenance & Evidence