Water → Ethyl 2-{[(furan-2-yl)methyl]amino}acetate

HRID 1511592Notes

Reaction equation

HRID 1511592 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].O>C1(C)C=CC=CC=1>[CH2:1]([NH:7][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3438FurfurylamineHCID 7751Ethyl chloroacetateHCID 8471Triethylamine

Product 1

HCID 13365154Ethyl 2-{[(furan-2-yl)methyl]amino}acetateYield 64.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Furfurylamine (15.0 g) and 17.2 g of triethylamine were dissolved in 75 mL of toluene, 20.8 g of ethyl chloroacetate was added thereto and the mixture was heated to reflux for 3 hours. After the reaction solution was cooled, 100 mL of water was added thereto and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 18.2 g of an objective compound as yellow liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter the reaction solution was cooled
  4. extractionthe mixture was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-766a7d625fb14b51bb74a5e5135533ff
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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