Acetic Acid → 3-(3-Nitrobenzyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-acetic acid

HRID 1416403Notes

Reaction equation

HRID 1416403 reaction equation
N1(CC([O-])=[O:9])C=CC=NC1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[CH2:17][N:18]1[C:22](=[O:23])C(=O)[N:20]([CH2:25][C:26](O)=O)[C:19]1=S)([O-:13])=[O:12].Cl.[C:34]([OH:37])(=[O:36])[CH3:35]>>[N+:11]([C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][CH:32]=1)[CH2:17][N:18]1[C:22](=[O:23])[CH:26]=[CH:25][N:20]([CH2:35][C:34]([OH:37])=[O:36])[C:19]1=[O:9])([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 106396263-(3-Nitrobenzyl)-4,5-dioxo-2-thioxoimidazolidine-1-acetic acidHCID 86754110Pyrimidine-1-acetate

Product 1

HCID 106859843-(3-Nitrobenzyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-acetic acid

Procedure

The above-prepared pyrimidine-1-acetate product of paragraph (2) (1.60 g), 6 mL of acetic acid and 2 mL of hydrochloric acid were mixed followed by heating to reflux for two hours. After concentration, it was heated to reflux for two hours more with 6 mL of acetic acid and 2 mL of hydrochloric acid. The solvent was evaporated therefrom and the residue was washed with water and recrystallized from ethanol to give 1.39 g of 3-(3-nitrobenzyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-acetic acid [Compound 16] as white crystals. The melting point, MS, IR, NMR, and elementary analysis for the compound were:

Workup

  1. temperatureby heating
  2. temperatureto reflux for two hours
  3. concentrationAfter concentration, it
  4. temperaturewas heated
  5. temperatureto reflux for two hours more with 6 mL of acetic acid and 2 mL of hydrochloric acid
  6. customThe solvent was evaporated
  7. washthe residue was washed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cdd3ebd91e1143aaa01d955c162c49e1
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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