Ethyl bromoacetate → HCID 12380728, compound

HRID 1639305Notes

Reaction equation

HRID 1639305 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:7]([NH:6][C:4]([C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:5])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2307552-amino-N-benzylbenzamide

Product 1

HCID 12380728HCID 12380728, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-N-benzylbenzamide (400 mg), ethyl bromoacetate (295 mg) and potassium carbonate (244 mg) in N,N-dimethylformamide (10 ml) was stirred at 100° C. for 17 hours. After cooling, the reaction mixture was poured into ice-cold water and extracted with diethyl ether. The extract was washed with water and dried. Removal of the solvent gave a residue, which was chromatographed on silica gel. Elution with chloroform gave ethyl 2-[2-(N-benzylcarbamoyl)anilino]acetate (137 mg).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into ice-cold water
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. customdried
  6. customRemoval of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform

Sources & evidence

ORD record
ord-d7aa0bad591f4344a75e45ef7e1e0ae2
Source dataset
uspto-grants-1989_11
Patent number
US04883800

Reaction notes

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