(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl)benzamide

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Reaction Steps

To a solution of N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide (0.10 g, 0.27 mmol) in tetrahydrofuran (10 mL) was added (methoxycarbonylsulfamoyl)-triethylammonium hydroxide (0.35 g, 0.63 mmol) at ambient temperature. The resulting solution was refluxed for 7 hours and concentrated in vacuo to dryness. The residue was purified by column chromatography to give N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl)benzamide (0.03 g 32%): mp 151-155° C.; 1H NMR (300 MHz, CDCl3) δ 9.03-9.00 (m, 2H), 8.41 (br s, 1H), 8.19-7.97 (m, 2H), 7.97-7.94 (m, 2H), 7.84-7.83 (m, 1H), 7.61-7.48 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 168.1, 167.6, 164.9, 154.7, 151.1, 135.9, 135.4, 134.7, 134.3, 131.3, 131.1, 129.4, 127.3, 125.4, 119.0, 112.9; MS (ES+) m/z 343.5 (M+1).

Provenance & Evidence