Furfural → Ethyl 3-[(furan-2-ylmethylene)amino]propanoate

HRID 1511599Notes

Reaction equation

HRID 1511599 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.Cl.[NH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

7

Reactant 4

HCID 7362FurfuralHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 68410140Ethyl 3-[(furan-2-ylmethylene)amino]propanoateYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Furaldehyde (10 g) was dissolved in 170 mL of methylene chloride, then 10 g of magnesium sulfate, 16 mL of triethylamine and 16 g of ethyl 3-aminopropionate hydrochloride were successively added thereto and the mixture was stirred overnight at room temperature. The reaction solution was poured over 100 mL of water, the mixture was subjected to extraction with methylene chloride and the solvent was evaporated therefrom in vacuo. The residue was dissolved in 100 mL of ethyl acetate, washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo to give 19.2 g of the objective compound as yellow liquid.

Workup

  1. extractionthe mixture was subjected to extraction with methylene chloride
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b8e12db1887a499a9302d71a70cd273b
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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