Lawesson's reagent → HCID 10225223, compound

Participants

Reaction Steps

To a stirred solution of 2-[4-(4-fluorobenzyl)piperidin-1-yl]-N-[2-oxo-2-(2-oxo-2,3-dihydrobenzothiazol-6-yl)ethyl]acetamide (0.50 g, 1.13 mmol) in 1,4-dioxan (30 mL) was added [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (Lawesson's reagent) (0.69 g, 1.70 mmol). The resulting suspension was heated at reflux for 24 hours. The reaction mixture was condensed to dryness in vacuo, redissolved in EtOAc, and washed with saturated aqueous sodium hydrogen carbonate, and saturated brine. The organic phase was dried (MgSO4) and condensed to dryness in vacuo. The material was then subject to column chromatography [silica gel, EtOAc/Heptanes (0-50% EtOAc over 60 min)] gave 6-{2-[4-(4-fluorobenzyl)piperidin-1-ylmethyl]thiazol-5-yl}-3H-benzothiazol-2-one (0.087 g, 18%) as an off-white solid:

Provenance & Evidence