Lawesson's reagent → 2-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-5-methyl-1,3,4-thiadiazole

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Reaction Steps

Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide] (271 mg) was added to a solution of N′2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazide (192 mg) [see Preparation 39] in toluene (10 ml). The reaction mixture was heated under reflux for 3 hours and the cooled mixture was then purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 30:70 (in 10% increments), by volume, hexane:ethyl acetate, to afford 2-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-5-methyl-1,3,4-thiadiazole (106 mg) as a clear oil.

Provenance & Evidence