Urea → 5-Nitrobarbituric acid

HRID 22468Notes

Reaction equation

HRID 22468 reaction equation
[N+:1]([CH:4]([C:8]([OH:10])=O)[C:5]([OH:7])=O)([O-:3])=[O:2].[NH2:11][C:12]([NH2:14])=[O:13]>>[CH:4]1([N+:1]([O-:3])=[O:2])[C:5](=[O:7])[NH:14][C:12](=[O:13])[NH:11][C:8]1=[O:10]

Participants

3

Reactant 2

HCID 1176UreaHCID 19816496Nitropropanedioic acid

Product 1

HCID 101955-Nitrobarbituric acid

Procedure

Nitration of malonic acid with acetyl nitrate in acetic acid/acetic anhydride was conducted to obtain nitromalonic acid. To the nitromalonic acid is added urea to obtain a condensation reaction mixture which is refluxed to form dilituric acid in situ. Various salts are separately prepared from the dilituric acid in situ using as cation sources potassium chloride, ammonia, and guanidinium chloride. The potassium diliturate salt, ammonium diliturate, guanidinium diliturate salts are each recovered and isolated by filtration.

Workup

  1. customto obtain
  2. customa condensation reaction mixture which
  3. temperatureis refluxed

Sources & evidence

ORD record
ord-bd51fb32c52b4bb2a2c762e7fe13783c
Source dataset
uspto-grants-1995_06
Patent number
US05428165

Reaction notes

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