Methanesulfonic Acid → HCID 21072792, compound

Participants

Reaction Conditions

Reaction Steps

9.7 g (25 mmol) N-tert-Butyl-4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-nicotinamide suspended in 48.5 ml toluene was heated to 95° C. and 24.0 g methanesulfonic acid was added dropwise giving an emulsion, which was stirred at 100° C. for two hours. After cooling to room temperature, the phases were separated and the organic phase was washed with deionized water. The combined aqueous phases were cooled to 0° C. and 28% aqueous sodium hydroxide was slowly added to increase the pH to ca. 12.5. The suspension obtained was extracted with dichloromethane. The combined organic extracts were dried and concentrated in a rotary evaporator. 100 ml Propyl acetate was added and the solution was concentrated in a rotary evaporator. A second portion of 100 ml propyl acetate was added and the solution was concentrated to ca. 23 g, forming a suspension to which 8.3 ml n-hexane was added. The suspension was stirred at 0° C. for one hour. The precipitate was filtered off, washed with n-hexane/propyl acetate 9:1 and dried in a vacuum oven to yield 8.0 g (97 %) 4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-nicotinamide as a light yellow powder of m.p.=198–202° C.

Provenance & Evidence