Triethylamine → 4-[5-{3-(2-Acetoxyethyl)ureido}methylfuran-2-yl]-2-(diaminomethyleneamino)thiazole

Participants

Reaction Steps

A mixture of 3-acetoxypropionic acid (2.5 g), diphenylphosphorylazide (4.3 ml) and triethylamine (2.6 ml) in dry benzene (50 ml) was stirred for an hour at 75° to 80° C. To the mixture was added to a mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (3.0 g) in a solution of tetrahydrofuran (45 ml) and methanol (45 ml) at ambient temperature, and the mixture was stirred for 2.5 hours at the same temperature. 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 4-[5-{3-(2-acetoxyethyl)ureido}methylfuran-2-yl]-2-(diaminomethyleneamino)thiazole (1.82 g).

Provenance & Evidence