Formic Acid → 2-(Diaminomethyleneamino)-4-(5-formamidomethylfuran-2-yl)thiazole

Participants

Reaction Steps

A mixture of acetic anhydride (2.4 ml) and formic acid (1.0 ml) was stirred for 30 minutes at 50° to 60° C. The above mixture was added to a mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (1.5 g) in tetrahydrofuran (15 ml) and N,N-dimethylformamide (15 ml) at ambient temperature and the mixture was stirred for 2.5 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate, tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with a brine and dried over magnesium sulfate. The solvent was removed by concentratoin in vacuo and the residue was recrystallized from a mixture of methanol, dioxane and tetrahydrofuran to give 2-(diaminomethyleneamino)-4-(5-formamidomethylfuran-2-yl)thiazole (0.80 g).

Provenance & Evidence