Sodium Iodide → 5-Chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole

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Reaction Steps

1.05 eq of NaI were dissolved in dry acetone. 1 eq of 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole, 1.03 eq of the thiophenol and 1 eq of Na2CO3 were added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with EtOAc and water. The organic phase was washed with an aqueous solution of Na2SO3 (sat), dried over MgSO4 and evaporated in vacuo. Preparative HPLC purification gave the 5-chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole. This was subsequently dissolved in 95% ethanol and conc. NH3 (aq) was added. In some cases acetonitrile was added in order to completely dissolve the starting material. The mixture was transferred to a microwave tube and run in the microwave at 150° C. for 5 min. the reaction was quenched with water and the desired 3-arylthiomethyl-5-amino-1,2,4-thiadiazole worked up and purified using standard procedures.

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