Ethylamine → HCID 3413435, compound

HRID 512102Notes

Reaction equation

HRID 512102 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-0eaff548d489476299d7233ea7145b2e
Source dataset
uspto-grants-2015_08
Patent number
US09102632B2

Reaction notes

Loading…