Lawesson's reagent → HCID 50992124, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (RS)-N-[3-(5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-4-chloro-benzamide (0.056 g, 0.2 mmol) in 1,2-dimethoxyethane (2 ml) was treated with Lawesson's reagent (0.083 g, 0.2 mmol). After heating to 70° C. the dispersion turned into solution; the temperature was kept during 16 hours. Another 0.5 eq of Lawesson's reagent were added to complete the reaction and heating was continued at 80° C. After 2 days the reaction was still incomplete. For the workup, the reaction mixture was evaporated to dryness and the residue directly purified by chromatography on an Isolute flash NH2 column using a gradient of dichloromethane/methanol=100/0 to 90/10 as the eluent. There were obtained 0.006 g (10% of theory) of (RS)-N-[3-(5-amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-4-chloro-thiobenzamide (27) as a yellow solid. Mass (calculated) C18H17ClFN3OS [377.87]; (found) [M+H]+=378.

Provenance & Evidence