Dimethylformamide → HCID 10318301, compound

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Reaction Steps

The mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (4.0 g), furfurylthioacetic acid (3.4 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.2 g) in N,N-dimethylformamide (40 ml) was stirred for 15 hours at ambient temperature. The mixture was added a mixture of ethyl acetate, tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with potassium carbonate. The separated organic layer was washed with a brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane, and isopropyl ether to give 2-(diaminomethyleneamino)-4-[5-{(furan-2-yl)methylthio}acetamidomethylfuran-2-yl]thiazole (3.50 g).

Provenance & Evidence