Hydrochloric Acid → 1-(4-t-Butylbenzyl)-3-[2-(4-methylthiazol-5-yl)ethyl]thiourea

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Reaction Steps

2-[2-(4-methylthiazol-5-yl)ethyl]isoindol-1,3-dione (3 g) was dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml) and to the solution was added dropwise hydrazine hydrate (610 mg), followed by stirring for 20 hours. To the obtained solution was added 2 N aqueous hydrochloric acid solution (6 ml), and the mixture was stirred for 3 hours and concentrated under reduced pressure to obtain reaction mixture (3.5 g) as a yellow solid. The obtained mixture (140 mg) was dissolved in dimethylformamide (5 ml) and to the solution were added 4-t-butylbenzylisothiocyanate (0.2 g) and a small amount of triethylamine, followed by stirring at room temperature for 21 hours. The resulting mixture was diluted with dichloromethane, washed with water, dried, concentrated under reduced pressure, and then purified by column-chromatography (hexane/ethyl acetate=1/1) to yield the compound 14-6 (0.07 g) as a liquid.

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