1-(3-Nitrobenzyl)urea → 5-Hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidine

HRID 1416396Notes

Reaction equation

HRID 1416396 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][NH:8][C:9]([NH2:11])=[O:10])([O-:3])=[O:2].C([O:22][CH:23](O)[C:24](OCC1C=CC=CC=1)=[O:25])C1C=CC=CC=1>C(O)(=O)C>[OH:25][CH:24]1[N:8]([CH2:7][C:6]2[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:9](=[O:10])[NH:11][C:23]1=[O:22]

Participants

4

Reactant 2

HCID 106554621-(3-Nitrobenzyl)ureaHCID 10849786HCID 10849786, compound

Product 1

HCID 108007195-Hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidineYield 48.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

N-(3-Nitrobenzyl)urea (78 g) was dissolved in 500 mL of 80% acetic acid, 120 g of benzyl 2-benzyloxy-2-hydroxyacetate was added thereto at 80° C. and the mixture was stirred at 80° C. for two hours. The mixture was concentrated in vacuo and the solvent was evaporated therefrom by means of an azeotropic distillation with toluene. The residue was purified by a silica gel column and recrystallized from a mixed solvent of ethyl acetate and hexane to give 49 g of 5-hydroxy-1-(3-nitrobenzyl)-2,4-dioxoimidazolidine.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe solvent was evaporated
  3. distillationby means of an azeotropic distillation with toluene
  4. customThe residue was purified by a silica gel column
  5. customrecrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-1d506d7c3c2a45958803af1d1b7115da
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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