2-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one → 7-Ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4,3,0]-nonan-5-ene-3,8-dione

HRID 21409Notes

Reaction equation

HRID 21409 reaction equation
C(=[N:8][N:9]=[C:10]1[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[CH2:12][N:11]1[CH2:22][C:23]([O:25]C)=O)C1C=CC=CC=1>Cl>[CH2:19]([O:18][C:16]([CH2:15][N:14]1[C:13](=[O:21])[CH2:12][N:11]2[C:10]1=[N:9][NH:8][C:23](=[O:25])[CH2:22]2)=[O:17])[CH3:20]

Participants

3

Reactant 1

HCID 541207212-Benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one

Product 1

HCID 229038087-Ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4,3,0]-nonan-5-ene-3,8-dioneYield 39.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 230 mg of 2-benzylidenehydrazono-3-ethoxycarbonylmethyl-1-methoxycarbonylmethylimidazolidin-4-one obtained in step (1) of Example 7 was added 10 ml of 0.5N hydrochloric acid, the mixture was subjected to a steam distillation for 40 minutes. The reaction mixture obtained was concentrated under reduced pressure, and the residue formed was charged on silica gel column chromatography and eluted with a mixture of chloroform and ethyl acetate at 1:2 by volume to obtain 60 mg of 7-ethoxycarbonylmethyl-1,4,5,7-tetraazabicyclo[4,3,0]-nonan-5-ene-3,8-dione.

Workup

  1. distillationthe mixture was subjected to a steam distillation for 40 minutes
  2. customThe reaction mixture obtained
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue formed
  5. additionwas charged on silica gel column chromatography
  6. washeluted with a mixture of chloroform and ethyl acetate at 1:2 by volume

Sources & evidence

ORD record
ord-9cd4bae540a144d6be1a0c3a4676b3bd
Source dataset
uspto-grants-1995_06
Patent number
US05422360

Reaction notes

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