Ethyl Acetate → HCID 19811405, compound

Temperature

5 °C

To a solution of N-(5-Chloro-2-nitrophenyl)-N',N'-dimethylethylenediamine (1.02 g) in ethyl acetate (10 ml) was added Raney nickel and the reaction mixture was stirred under a hydrogen atmosphere at atmospheric pressure at 5° C. for 1 hour. The reaction mixture was then filtered and the solvent was distilled off under reduced pressure. The residue was dissolved in dichloromethane (15 ml), followed by dropwise addition of triethylamine (1.28 g) and ethyl chloroformate (1.14 g) in turn at 5° C. with stirring. The reaction mixture was further stirred at room temperature for 1 hour and diluted with water (10 ml). The organic layer was washed with 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 1.05 g of N-(5-chloro-2-ethoxycarbonylaminophenyl)-N-ethoxycarbonyl-N',N'-dimethylethylenediamine.

1. filtrationThe reaction mixture was then filtered
2. distillationthe solvent was distilled off under reduced pressure
3. dissolutionThe residue was dissolved in dichloromethane (15 ml)
4. additionfollowed by dropwise addition of triethylamine (1.28 g) and ethyl chloroformate (1.14 g) in turn at 5° C.
5. stirringwith stirring
6. stirringThe reaction mixture was further stirred at room temperature for 1 hour
7. additiondiluted with water (10 ml)
8. washThe organic layer was washed with saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous sodium sulfate
10. distillationThe solvent was distilled off under reduced pressure
11. customthe residue was purified by silica gel chromatography (eluent:chloroform:methanol=50:1)

ORD record

ord-054e432c658e4416aca2616c87c4bc84

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05162318