Diethyl iminodiacetate → 2-Benzylidenehydrazono-1-methoxycarbonylmethylimidazolidin-4-one

HRID 1489134Notes

Reaction equation

HRID 1489134 reaction equation
C[O-].[Na+].[Na].[CH:5](=[N:12][NH:13][C:14](N)=[NH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O[C:20](=[O:29])[CH2:21][NH:22][CH2:23][C:24]([O:26][CH2:27]C)=[O:25])C>CO.C(Cl)(Cl)Cl.O>[CH:5](=[N:12][N:13]=[C:14]1[NH:15][C:20](=[O:29])[CH2:21][N:22]1[CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 80502Diethyl iminodiacetateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 178513139HCID 178513139, compound

Product 1

HCID 1360406052-Benzylidenehydrazono-1-methoxycarbonylmethylimidazolidin-4-oneYield 27.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a methanol solution of sodium methoxide prepared by dissolving 2.30 g of metal sodium in 150 ml of methanol was added 5.70 g of benzylideneaminoguanidine, and, after stirring the mixture for one hour at room temperature, 11.35 g of iminodiacetic acid diethyl ester was added thereto, followed by refluxing under heating for 17 hours. After cooling the reaction mixture, water and chloroform were added thereto to distribute the mixture between aqueous and organic layers and, then, the aqueous layer was extracted three times with chloroform. The organic layer was combined with the extract. After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure, and the residue was charged on silica gel column chromatography, followed by elution with a mixed solvent of chloroform and methanol (100:1 (v/v)). Thus 2.61 g of 2-benzylidenehydrazono-1-methoxycarbonylmethylimidazolidin-4-one was obtained.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 17 hours
  3. additionwere added
  4. extractionthe aqueous layer was extracted three times with chloroform
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionthe residue was charged on silica gel column chromatography
  8. washfollowed by elution with a mixed solvent of chloroform and methanol (100:1 (v/v))

Sources & evidence

ORD record
ord-42be6173687f454a955d4788289f00de
Source dataset
uspto-grants-1997_10
Patent number
US05677322

Reaction notes

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