Ethylenediamine → ethyl 4-(4,5-dihydro-1H-imidazol-2-yl)benzoate

HRID 352783Notes

Reaction equation

HRID 352783 reaction equation
Cl.C(O[N:5]=[CH:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)C.[CH2:18](N)[CH2:19][NH2:20]>C(O)C>[NH:20]1[CH2:19][CH2:18][N:5]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 73992977Ethyl 4-[1-(ethoxy)iminomethyl]benzoate hydrochloride

Product 1

HCID 22709787ethyl 4-(4,5-dihydro-1H-imidazol-2-yl)benzoateYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The resulting ethyl 4-[1-(ethoxy)iminomethyl]benzoate hydrochloride (2.00 g) was dissolved in ethanol (30 ml). Under ice cooling, ethylenediamine (0.52 ml) was added to the resulting solution, followed by heating to room temperature. The reaction mixture was stirred overnight. To the residue obtained by distilling off the solvent under reduced pressure, dilute hydrochloric acid was added to make it acidic, followed by concentration again. The residue was purified by chromatography through a synthetic adsorbent (“Diaion HP-20”, trade name; water˜50% acetonitrile-water). Solution of hydochloride in ethanol was added to the resulting fraction and the mixture was concentrated. Colorless crystalline powder precipitated by the addition of tetrahydrofuran was collected by filtration and dried, whereby the title compound (1.63 g, 19%) was obtained.

Workup

  1. customTo the residue obtained
  2. distillationby distilling off the solvent under reduced pressure, dilute hydrochloric acid
  3. additionwas added
  4. concentrationfollowed by concentration again
  5. customThe residue was purified by chromatography through a synthetic adsorbent (“Diaion HP-20”, trade name; water˜50% acetonitrile-water)
  6. additionSolution of hydochloride in ethanol was added to the resulting fraction
  7. concentrationthe mixture was concentrated
  8. customColorless crystalline powder precipitated by the addition of tetrahydrofuran
  9. filtrationwas collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-ff087d32c8ed47359c453f9c1a4f1ce5
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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