Hydrochloric Acid → 1-Benzyl-2,4-dioxoimidazolidine-3-acetic acid

HRID 1416389Notes

Reaction equation

HRID 1416389 reaction equation
NC(N)=[O:3].[N+]([C:8]1[CH:9]=[C:10]([CH:24]=[CH:25][CH:26]=1)[CH2:11][N:12]1[C:16](=O)[C:15](=[O:18])[N:14]([CH2:19][C:20]([OH:22])=[O:21])[C:13]1=C)([O-])=O.Cl>C(O)(=O)C>[CH2:11]([N:12]1[CH2:16][C:15](=[O:18])[N:14]([CH2:19][C:20]([OH:22])=[O:21])[C:13]1=[O:3])[C:10]1[CH:24]=[CH:25][CH:26]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 10638264HCID 10638264, compound

Product 1

HCID 225745971-Benzyl-2,4-dioxoimidazolidine-3-acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.7 g of the above-prepared urea product of paragraph (1) dissolved in 3 mL of acetic acid and 1 mL of concentrated hydrochloric acid was heated to reflux for four hours. After evaporating the solvent therefrom, 3 mL of acetic acid and 1 mL of concentrated hydrochloric acid were added to the residue followed by stirring for two hours. The resulting component was concentrated, washed well with water and recrystallized from ethanol to give 1.2 g of 1-benzyl-2,4-dioxoimidazolidine-3-acetic acid [Compound 3]. The melting point, MS, IR, NMR, and elementary analysis for the compound were:

Workup

  1. temperatureto reflux for four hours
  2. customAfter evaporating the solvent
  3. addition3 mL of acetic acid and 1 mL of concentrated hydrochloric acid were added to the residue
  4. concentrationThe resulting component was concentrated
  5. washwashed well with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-edd140126e494c95aca71820828ec624
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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