Methyl iodide → 2-(2,6-Dichlorophenylamino)-4,6-dimethyl-1H-thieno[3,4-d]imidazole hydrochloride

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Reaction Steps

0.664 g of methyl iodide was added to a solution of 0.27 g of N-(3-amino-2,5-dimethyl-4-thienyl)-N′-(2,6-dichlorophenyl)thiourea in 30 ml of anhydrous ethanol and the mixture was boiled under reflux conditions for approx. 10 hours. After the solvent had been distilled off on a Rotavapor, the residue was admixed with water and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was distilled off on a Rotavapor. The residue was then purified by column chromatography on silica gel using a mixture of 20 parts by volume of ethyl acetate, 10 parts by volume of n-heptane, 3 parts by volume of glacial acetic acid. After the solvent had been distilled off, the residue was dissolved in a little ethyl acetate, made strongly acidic using a hydrogen chloride gas-saturated diethyl ether solution, and the amorphous precipitate was fully crystallized by heating. M.p. 270–273° C.

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