Methyl iodide → 4H-1,2,4-Triazole, 4-methyl-3-(methylthio)-5-(2-thienyl)-

Participants

Reaction Steps

A solution of methyl iodide (6.3 ml, 1.0×10-1 mole) in ethanol (32 ml) was added dropwise to a stirred, room temperature solution of 2,4-dihydro-4-methyl-5-(2-thienyl)-3H-1,2,4-triazole-3-thione (12.5 g, 6.34×10-2 mole) and 1 molar aqueous NaOH (142 ml, 1.42×10-1 mole). After being stirred for about 14 hours the reaction was extracted four times with EtOAc. The EtOAc extracts were combined, washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure giving a tacky yellow solid which was purified by flash chromatography (EtOAc). Crystallization from EtOAc gave colorless crystals: 10.5 g (78%), mp 83°-85° C.

Provenance & Evidence