Ethylamine → HCID 3413435, compound

HRID 474182Notes

Reaction equation

HRID 474182 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>[CH2:8]([O:7][C:5](=[O:6])[C:4]([NH:13][CH2:11][CH3:12])=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 7268Diethyl Oxalate

Product 1

HCID 3413435HCID 3413435, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 135.8 ml (1000 mM) of diethyloxalate and 1 g of aliquat 336 in 1000 ml of dichloromethane were added 64.4 ml (1000 mM) of ethylamine (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, wick 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. Yield: 41.3%.

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, wick
  4. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea84d4a722e7468fbc5e50e828948512
Source dataset
uspto-grants-2014_01
Patent number
US08637522B2

Reaction notes

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