Ethyl bromoacetate → HCID 131717330, compound

HRID 1195083Notes

Reaction equation

HRID 1195083 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])#[N:2].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:17](=[O:20])(O)[O-].[Na+]>C(O)C>[C:17]([N:5]([C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[C:1]#[N:2])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:20])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 729132-AminobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 131717330HCID 131717330, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-cyanoaniline (59g), ethyl bromoacetate (90g) and sodium bicarbonate (50g) were refluxed in ethanol (500ml), with stirring, for 42 hours. The reaction mixture was cooled slightly, filtered, and the filtrate cooled. The solid which formed was removed by filtration. Evaporation left an oil, containing unreacted starting material and the desired product, N-(2-cyanophenyl) glycine, ethyl ester. Trituration with ethanol and cooling gave the required product which after filtering was crystallized from ethanol.

Workup

  1. temperatureThe reaction mixture was cooled slightly
  2. filtrationfiltered
  3. temperaturethe filtrate cooled
  4. customThe solid which formed
  5. customwas removed by filtration
  6. customEvaporation
  7. waitleft an oil
  8. additioncontaining unreacted
  9. temperatureTrituration with ethanol and cooling

Sources & evidence

ORD record
ord-71336d76c028434d8ff063323ddb19f0
Source dataset
uspto-grants-1992_05
Patent number
US05110348

Reaction notes

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