Water → HCID 10341350, compound

Participants

Reaction Steps

A mixture of 2-(diaminomethyleneamino)-4-[5-{(furan-2-yl)methylthio}acetamidomethylfuran-2-yl]thiazole (1.5 g) and 3-chloroperbenzoic acid (0.9 g) in a mixture of tetrahydrofuran (30 ml) and N,N-dimethylformamide (10 ml) was stirred for 1.5 hours at ambient temperature. To the reaction mixture was added a solution of water and ethyl acetate and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with 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)methylsulfinyl}acetamidomethylfuran-2-yl]thiazole (1.5 g).

Provenance & Evidence