反应详情

A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (3.0 g), triethylamine (3.5 ml) and ethyl ethanesulfonylformimidate (1.5 g) in methanol (60 ml) was stirred at ambient temperature for 6.5 hours and after solvent was removed by concentration in vacuo. To the residue was added a mixture of tetrahydrofuran, ethyl acetate and water 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 the solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform 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 diisopropyl ether to give 2-(diaminomethyleneamino)-4-(6-ethanesulfonyliminomethylaminomethylpyridin-2-yl)thiazole (0.88 g).

1. customafter solvent was removed by concentration in vacuo
2. additionTo the residue was added
3. additiona mixture of tetrahydrofuran, ethyl acetate and water
4. washThe separated organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. customEvaporation of the solvent
7. customgave a residue, which
8. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (9:1, V/V)
9. additionThe eluted fractions containing the desired product
10. customwere collected
11. customevaporated in vacuo
12. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether