Ethyl bromoacetate → 66935-31-7

HRID 839857Notes

Reaction equation

HRID 839857 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1C=CC=CC=1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 80182-MethoxyethylamineHCID 8471Triethylamine

Product 1

HCID 1581881566935-31-7Yield 75.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 165.2 g of 2-methoxyethylamine and 202.4 g of triethylamine in 1 l of benzene was added dropwise a solution of 334.0 g of ethyl bromoacetate in 200 ml of benzene in one hour at room temperature. At the end of this period, the mixture was heated at reflux for 2 hours to complete the reaction. Upon chilling, the triethylamine hydrobromide was removed by filtration and washed with benzene. After removal of the solvent, the product was distilled in vacuo to yield 242.8 g (75.3 percent) of N-(2-methoxyethyl)glycine ethyl ester, B.P. 73°-5° C/4 mmHg. The following amino acid ethyl esters not previously reported in the chemical literature were synthesized by the aforementioned procedure which is essentially that as taught by A. J. Speziale et al., J. Org. Chem., 25 731 (1960).

Workup

  1. temperatureAt the end of this period, the mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe reaction
  4. temperatureUpon chilling
  5. customthe triethylamine hydrobromide was removed by filtration
  6. washwashed with benzene
  7. customAfter removal of the solvent
  8. distillationthe product was distilled in vacuo

Sources & evidence

ORD record
ord-19e0ab8a6d49487e8d672ebd2a869732
Source dataset
uspto-grants-1978_06
Patent number
US04097472

Reaction notes

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