Hydrochloric Acid → 5-Hydroxy-3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetic acid

HRID 1416401Notes

Reaction equation

HRID 1416401 reaction equation
[O:1]=C1CN(CC([O-])=O)C(=O)N1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[CH2:18][N:19]1[C:23](=[O:24])[C:22](=[O:25])[N:21]([CH2:26][C:27]([OH:29])=[O:28])[C:20]1=S)([O-:14])=[O:13].Cl>C(O)(=O)C>[OH:25][CH:22]1[N:21]([CH2:26][C:27]([OH:29])=[O:28])[C:20](=[O:1])[N:19]([CH2:18][C:17]2[CH:31]=[CH:32][CH:33]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:23]1=[O:24]

Participants

5

Reactant 3

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

Product 1

HCID 106385905-Hydroxy-3-(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) (15 g) was suspended in a mixed solvent of acetic acid and hydrochloric acid and the mixture was heated to reflux with stirring for two hours. Then the mixture was concentrated in vacuo, ether-chloroform was added thereto. The crystals were dislodged from the wall of the reaction flask with a spatula. The solid was washed with ether and recrystallized from a mixed solvent of ethanol and water to give 8.1 g of 5-hydroxy-3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetic acid [Compound 15]. The melting point, MS, IR, NMR, and elementary analysis for the compound were:

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. concentrationThen the mixture was concentrated in vacuo, ether-chloroform
  4. additionwas added
  5. washThe solid was washed with ether
  6. customrecrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-e290105a68214f799ce679b4b7df143e
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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