[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH:14][C:15](=[O:17])[CH3:16])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O>C(#N)C.O>[C:1]1([S:7]([CH2:10][C:11]2[O:17][C:15]([CH3:16])=[N:14][N:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1To a stirred solution of 1.40 g (5.5 mmol) of acetic acid N′-(2-benzenesulfonyl-acetyl)-hydrazide in 50 mL of acetonitrile, 1.02 g (6.5 mmol, 1.2 eq) of phosphorus oxychloride were added, and the solution heated at reflux for 3 hours. The reaction mixture was diluted with water, extracted with EtOAc, the organic phase dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with EtOAc yielded 0.90 g (70%) of 2-benzenesulfonylmethyl-5-methyl-[1,3,4]oxadiazole as a white solid, MS: 239 (MH+).
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