Lawesson's reagent → 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of N′-benzoyl-3-iodo-1-tosyl-1H-indole-5-carbohydrazide (1.29 g, 2.31 mmol) in dioxane (24 mL) at RT was added Lawesson's Reagent (1.40 g, 3.46 mmol) (Aldrich). The solution was heated to 110° C. for 3 h. The mixture was concentrated and the residue was purified with flash chromatography (eluting with 0-60% EtOAc in Hex) to give 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-phenyl-1,3,4-thiadiazole (518 mg, 40%) as a light yellow-orange crystalline solid after washing with Et2O. MS (ESI, pos. ion) m/z: 557.9 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 7.96-8.10 (5H, m), 7.81 (2H, d, J=8.4 Hz), 7.77 (1H, s), 7.48-7.55 (3H, m), 7.28 (2H, d, J=8.2 Hz), 2.37 (3H, s).

Provenance & Evidence