Hydrochloric Acid → 3-(3-Nitrobenzyl)-2,4-dioxoimidazolidine-1-acetic acid

HRID 1416393Notes

Reaction equation

HRID 1416393 reaction equation
[O:1]=[C:2]1[CH2:6][N:5]([CH2:7][C:8]([O-:10])=[O:9])[C:4](=[O:11])[NH:3]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[CH2:18]N1C(=O)C(=O)N(CC(O)=O)C1=S)([O-:14])=[O:13].Cl>C(O)(=O)C>[N+:12]([C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[CH2:18][N:3]1[C:2](=[O:1])[CH2:6][N:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4]1=[O:11])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7219893HCID 7219893, compoundHCID 106396263-(3-Nitrobenzyl)-4,5-dioxo-2-thioxoimidazolidine-1-acetic acid

Product 1

HCID 105656263-(3-Nitrobenzyl)-2,4-dioxoimidazolidine-1-acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The above-prepared dioxoimidazolidine-1-acetate product of paragraph (2) from several production runs (1.7 g) was heated to reflux in a mixed solvent of 12 mL of acetic acid and 4 mL of concentrated hydrochloric acid for one hour. After evaporating the solvent therefrom, 12 mL of acetic acid and 4 mL of concentrated hydrochloric acid were added to the residue and the mixture was heated to reflux for one hour more. The refluxed mixture was poured over a mixed solution of ethyl acetate and 10% sodium hydroxide, the mixture was extracted with 10% sodium hydroxide several times and the resulting aqueous extract was subjected to a reverse extraction several times. The extracts were combined, dried over sodium sulfate, concentrated and recrystallized from ethanol to give 350 mg of 3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetic acid [Compound 6]. The melting point, MS, IR, NMR, and elementary analysis for the compound were:

Workup

  1. customAfter evaporating the solvent
  2. addition12 mL of acetic acid and 4 mL of concentrated hydrochloric acid were added to the residue
  3. temperaturethe mixture was heated
  4. temperatureto reflux for one hour more
  5. additionThe refluxed mixture was poured over a mixed solution of ethyl acetate and 10% sodium hydroxide
  6. extractionthe mixture was extracted with 10% sodium hydroxide several times
  7. extractionthe resulting aqueous extract
  8. extractionwas subjected to a reverse extraction several times
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a8b954a55b1c4f3a837b73be00ea35e5
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

Loading…