反应详情

A mixture of 5-nitro-1H-benzoimidazol-2-thiol (1.95 g, 0.01 mol), 4-bromomethyl-benzoic acid methyl ester (2.29 g, 0.01 mol), triethylamine (2 mL), and ethanol (100 mL) was heated at reflux for a period of 4.5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with water. The organic phase was evaporated. The residue was crystallized from ethyl acetate/hexane. The solid obtained was dissolved in methanol and the solution was saturated with hydrogen chloride. The methanol was evaporated. The residue was treated with ethyl acetate. The solid was collected to give the title compound (1.4 g, 41%) as a mono-hydrochloride, white solid, m.p. 228°-230° (dec.). Anal. Calcd. for C16H13N3O4S.HCl: C, 50.60; H, 3.72; N, 11.06. Found: C, 50.82; H, 3.68; N, 10.92. Mass spectrum (+FAB; [M+H]+) 344. 1H-NMR (DMSO-d6 ; 400 MHz) δ 8.32 (s, 1H), 8.06 (d, 1H), 7.88 (d, 2H), 7.62 (m, 3H), 5.0-7.4 f(br s, 4H), 4.67 (s, 2H), and 3.81 ppm (s, 3H).

1. temperaturewas heated
2. temperatureat reflux for a period of 4.5 hours
3. customThe solvent was evaporated
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with water
6. customThe organic phase was evaporated
7. customThe residue was crystallized from ethyl acetate/hexane
8. customThe solid obtained
9. customThe methanol was evaporated
10. additionThe residue was treated with ethyl acetate
11. customThe solid was collected