Dichloromethane → HCID 9798650, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g (3.0 mmole) of N-({3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-4,5-dihydro-5-isoxazolyl}methyl)acetamide is suspended in 12 ml dioxane in a 50 ml one neck round bottom flask under nitrogen. The suspension is treated with Lawesson's Reagent (1.27 g, 3.15 mmole) and the reaction is stirred at 80° C. for 1 hour. The mixture is cooled to room temperature, brought to homogeneity with dichloromethane and is treated with 10 g silica gel (230-400 mesh) and is concentrated to dryness. The plug is loaded onto a SIM and the material is chromatographed twice over 40 g silica gel (BIOTAGE), eluting with 7% acetone/dichloromethane while collecting 25 ml fractions. Fractions 6-13 are combined and concentrated to afford 902 mg (85%) of the title compound as a solid. mp=219-220° C.

Provenance & Evidence