Dihydrouracil → 1,3-Diacetyldihydropyrimidine-2,4(1H,3H)-dione

HRID 2420219Notes

Reaction equation

HRID 2420219 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[NH:6]1[CH2:13][CH2:12][C:10](=[O:11])[NH:9][C:7]1=[O:8].[CH2:14]=[C:15]=[O:16]>C(OCC)(=O)C>[C:15]([N:6]1[CH2:13][CH2:12][C:10](=[O:11])[N:9]([C:1](=[O:4])[CH3:2])[C:7]1=[O:8])(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 649DihydrouracilHCID 10038KeteneHCID 517045Sodium Acetate

Product 1

HCID 542125861,3-Diacetyldihydropyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After adding 1.5 gm of finely pulverized sodium acetate suspended in 1 liter of ethyl acetate, 15 gm (0.13 mol) of 5,6-dihydrouracil were reacted with ketene at boiling temperature (77° C). After the reaction had been completed, the catalyst was filtered off and the solvent was distilled off under reduced pressure. The residue was recrystallized from isopropanol. The melting point was 81.5° C to 83° C, and the elementary analysis resulted in the following values:

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was recrystallized from isopropanol
  4. customThe melting point was 81.5° C to 83° C, and the elementary analysis resulted in the following values

Sources & evidence

ORD record
ord-437491beecc04c0abe71ae455a22fc55
Source dataset
uspto-grants-1978_08
Patent number
US04110242

Reaction notes

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