反应详情

1-(Bromomethyl)-4-nitrobenzene (1.9 g), triphenylphosphine (2.31 g) and N,N-dimethylformamide (20 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2.5 hours. Then potassium tert-butoxide (1.19 g) and N-(4-formyl-1,3-thiazol-2-yl)acetamide (1.5 g) were added and the mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1N-hydrochloric acid, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (1:1)-→(1:2) as an eluent, and triturated with ethyl ether to give N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (1.59 g) as a yellow solid.

1. stirringthe mixture was stirred at room temperature for 14 hours
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with 1N-hydrochloric acid, water and saturated sodium chloride solution
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (1:1)-→(1:2) as an eluent
7. customtriturated with ethyl ether