Ethylamine → HCID 3413435, compound

HRID 589561Notes

Reaction equation

HRID 589561 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

HCID 6341EthylamineHCID 7268Diethyl Oxalate

Product 1

HCID 3413435HCID 3413435, compoundYield 41.3%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

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

  1. dry with materialThe reaction mixture was dried over anhydrous sodium sulfate
  2. customthe solvent was removed under vacuum
  3. customto give an oil, which
  4. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-812a316a3011465992534bb09b6bbc15
Source dataset
uspto-grants-2016_01
Patent number
US09233937B2

Reaction notes

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