Ethyl Methanesulfonate → HCID 178477475, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-(2-((Phenylmethyl)(methyl)amino)ethyl)phenyl)-2-thiourea (step (f), 0.30 g) was suspended in 200 ethanol (2.5 ml), and the mixture was treated with methanesulfonic acid (0.065 ml) and then ethyl methanesulfonate (0.12 ml). After 3 hours at 100° C., TLC on C18 silica with 80% methanol/20% water with 0.8% ammonium acetate showed incomplete conversion to product. At this point additional ethyl methanesulfonate (0.20 g) was added and the mixture refluxed for one hour. After stirring overnight, the crude reaction product was treated with ethyl acetate (50 ml) and water (50 ml). The aqueous layer was treated with sodium carbonate (0.25 g) and extracted with diethyl ether (20 ml). The remaining aqueous layer was treated with sodium bicarbonate (1 g) and extracted with of diethyl ether (20 ml). The ether layers were identical by TLC and were combined, dried with sodium sulfate and evaporated to yield the free base which was then treated with maleic acid (0.24 g) in methanol (1 ml), then diluted with ethyl acetate (4 ml) followed by diethyl ether (25 ml), giving an oil. The solvents were decanted, and the resulting solids were dissolved in hot isopropanol (20 ml) and cooled to -20° C. The resulting solids were collected and air dried to provide N-(4-(2-((phenylmethyl)(methyl)amino)ethyl)phenyl) carbamimidothioic acid, ethyl ester, 0.34 g, m.p. 136°-137° C.

Provenance & Evidence