Dimethylamine → N,N,1,2-Tetramethylhydrazine-1-carboxamide

To a solution of N-benzyloxycarbonyl-N,N'-dimethylhydrazine (1.6 g) in toluene (30 ml) was added trichloromethyl chloroformate (0.553 ml). After the solution was refluxed for 30 minutes, dimethylamine (672 mg) and triethylamine (2.0 g) was added thereto at 0° C. The reaction mixture was stirred at ambient temperature for 2 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (50 ml). The solution was washed with 5% hydrochloric acid, 1M sodium bicarbonate solution and water successively, and dried over magnesium sulfate. After evaporation of the solvent, the residue was dissolved in methanol (20 ml) and water (20 ml). The solution was hydrogenated over 10% palladium on carbon (100 mg) at 3 atmospheric pressure of hydrogen for 1 hour. The solution was filtered and concentrated in vacuo to give N-(N,N-dimethylcarbamoyl)-N,N'-dimethylhydrazine (820 mg) as an oil.

1. temperatureAfter the solution was refluxed for 30 minutes
2. customat 0° C
3. customAfter evaporation of the solvent
4. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
5. washThe solution was washed with 5% hydrochloric acid, 1M sodium bicarbonate solution and water successively
6. dry with materialdried over magnesium sulfate
7. customAfter evaporation of the solvent
8. dissolutionthe residue was dissolved in methanol (20 ml)
9. waitThe solution was hydrogenated over 10% palladium on carbon (100 mg) at 3 atmospheric pressure of hydrogen for 1 hour
10. filtrationThe solution was filtered
11. concentrationconcentrated in vacuo

ORD record

ord-fa644895c028490e9589dd5164fd0f72

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05223489