Ethyl bromoacetate → 66935-31-7

HRID 616364Notes

Reaction equation

HRID 616364 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 to a solution of 334.0 g of ethyl bromoacetate in 200 ml of benzene in 1 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 hydrochloride 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.

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 hydrochloride 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-9c8ff7d65bcb484b9a3e3b7ed63c0779
Source dataset
uspto-grants-1978_02
Patent number
US04073892

Reaction notes

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