Lawesson's reagent → (R)-5-[5-(Benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholine-3-thione

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-one (1.53 g, 3.94 mmol) in dioxane (30 ml) was treated with Lawesson's reagent (1.3 g, 3.15 mmol). The orange coloured suspension was heated in a sealed tube at 80° C. for 18 hours. For the workup, the meanwhile green coloured reaction mixture was evaporated at reduced pressure and the residue directly purified by flash chromatography on a silica-amine phase using a gradient of heptane/ethyl acetate=100:0 to 40:60 as the eluent. The (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-methyl-morpholin-3-thione was obtained as a yellow solid (0.803 g, 50%); (calculated) C24H21FN2OS [404.51]; (found) [M+H]+=405.

Provenance & Evidence