反应详情

温度

50 °C

To a solution of 3-(3-chloro-propoxy)-benzoic acid ethyl ester (5.50 g, 22.7 mmol) in DMF (150 ml) at rt was added Cs2CO3 (14.8 g, 45.5 mmol) and 1,3-dihydro-benzoimidazol-2-ylidene amine (2.75 g, 20.7 mmol). The reaction was heated to 50° C. for 12 h. After this time, the resulting mixture was cooled to rt and partitioned between EtOAc and H2O. The organic layer was separated and the aqueous phase was extracted with additional EtOAc. The combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated under redcued pressure. The crude product was purified by chromatography on silica eluting with 2% MeOH/dichloromethane to give 3-[3-(2-imino-2,3-dihydro-benzoimidazol-1-yl)-propoxy]-benzoic acid ethyl ester (4.9 g g, 64%). HPLC-MS 340 [M+1]+.

1. temperatureAfter this time, the resulting mixture was cooled to rt
2. custompartitioned between EtOAc and H2O
3. customThe organic layer was separated
4. extractionthe aqueous phase was extracted with additional EtOAc
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under redcued pressure
9. customThe crude product was purified by chromatography on silica eluting with 2% MeOH/dichloromethane