Dioxoimidazolidine-3-acetate → 5-Hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidine-3-acetic acid

HRID 1416398Notes

Reaction equation

HRID 1416398 reaction equation
[O:1]=C1CNC(=O)N1CC([O-])=O.[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.O1CCOCC1>[OH:24][CH:23]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:20](=[O:1])[N:21]([CH2:26][C:27]([OH:29])=[O:28])[C:22]1=[O:25]

Participants

5

Reactant 2

HCID 2512551Dioxoimidazolidine-3-acetateHCID 106396263-(3-Nitrobenzyl)-4,5-dioxo-2-thioxoimidazolidine-1-acetic acid

Product 1

HCID 108523655-Hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidine-3-acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The above-prepared dioxoimidazolidine-3-acetate product of paragraph (2) (3.6 g) was dissolved in a mixed solvent of 4N hydrochloric acid and dioxane and the solution was stirred at room temperature for six hours. The reaction solution was concentrated in vacuo to dryness and then chloroform was added to the residue. The crystals were dislodged from the wall of the reaction flask with a spatula. The solid was collected by filtration, washed with chloroform and dried to give 0.8 g of 5-hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidine-3-acetic acid [Compound 14] as amorphous crystals. The melting point, MS, IR, NMR, and elementary analysis for the compound were:

Workup

  1. concentrationThe reaction solution was concentrated in vacuo to dryness
  2. additionchloroform was added to the residue
  3. filtrationThe solid was collected by filtration
  4. washwashed with chloroform
  5. customdried

Sources & evidence

ORD record
ord-d44e976853a54eb69ddafa30fea329b5
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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