Ethylamine → Ethyl (ethylamino)(oxo)acetate
Reaction equation
C(O[C:4](=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.[CH2:11]([NH2:13])[CH3:12]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl.O>[CH2:8]([O:7][C:5](=[O:6])[C:4]([NH:13][CH2:11][CH3:12])=[O:10])[CH3:9]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To 135,8 ml (1000 mM) of diethyloxalate and 1 g of aliquat 336, in 1000 ml of dichloromethane, were added 64 ml (1000 mM) of ethylamine at 70% in water. The reaction mixture was stirred at room temperature for 72 h. The reaction mixture was dried over anhydrous sodium sulfate and the solvent was removed under vacuum to give an oil, which was further purified by silica gel column chromatography, using dichloromethane/dimethylketone (95/5) as eluant, to give 59.9 g of ethyl(ethyl amino)(oxo)acetate as an oil.
Workup
- dry with materialThe reaction mixture was dried over anhydrous sodium sulfate
- customthe solvent was removed under vacuum
- customto give an oil, which
- customwas further purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-e47a50fc6abd494a8d53261589d26157
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815859B2
Reaction notes
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