反应详情

To a solution of N-(2-ethoxycarbonylaminophenyl)-N',N'-dimethylethylenediamine (0.94 g) in methanol (20 ml) and dichloromethane (30 ml) were added calcium carbonate (0.40 g) and benzyltrimethylammonium tribromide (1.46 g). The reaction mixture was stirred at room temperature for 1.5 hours. The insoluble matter was then filtered off and the solvent was distilled off under reduced pressure. The residue was diluted with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was dissolved in chloroform (30 ml). To the solution was added ethyl chloroformate (0.53 g) dropwise, and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was successively washed with 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:chloroform:methanol=50:1) to give 0.95 g of N-(4-bromo-2-ethoxycarbonylaminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine.

1. filtrationThe insoluble matter was then filtered off
2. distillationthe solvent was distilled off under reduced pressure
3. additionThe residue was diluted with 1N aqueous sodium hydroxide solution
4. extractionextracted with ethyl acetate
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. distillationthe solvent was distilled off
7. dissolutionthe residue was dissolved in chloroform (30 ml)
8. additionTo the solution was added ethyl chloroformate (0.53 g) dropwise
9. stirringthe reaction mixture was stirred at room temperature for 5 hours
10. washThe reaction mixture was successively washed with 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
11. dry with materialdried over anhydrous sodium sulfate
12. distillationThe solvent was distilled off under reduced pressure
13. customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=50:1)