Urea → Octyl barbituric acid

HRID 993070Notes

Reaction equation

HRID 993070 reaction equation
[Na].[CH2:2]([CH:10]([C:16]([O:18]CC)=O)[C:11]([O:13]CC)=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:21][C:22]([NH2:24])=[O:23]>C(O)C>[CH2:2]([CH:10]1[C:11](=[O:13])[NH:24][C:22](=[O:23])[NH:21][C:16]1=[O:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 1176UreaHCID 252340Diethyl octylmalonateHCID 5360545Sodium

Product 1

HCID 260794Octyl barbituric acidYield 75.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium (5.32 g) in 400 ml of anhydrous ethanol is added a solution of diethyl 2-octylmalonate (31.5 g) in 50 ml of ethanol and successively 10.27 g of urea, then the mixture is refluxed for 2 hours 30 minutes. The mixture is rapidly cooled to room temperature and the solid which was formed is recovered by filtration and washed with diethyl ether. The solid is then dissolved in 200 ml of water and acidified with 6 N hydrochloric acid until pH 1.5-2 is reached. A solid separates. The mixture is added with 200 ml of ethyl acetate and it is stirred for 2 hours, then it is added with additional 800 ml of warm ethyl acetate. The organic phase is separated and the aqueous phase is washed with 200 ml of ethyl acetate. The pooled organic phases are washed with 250 ml of saturated aqueous solution of sodium chloride dried over sodium sulfate and concentrated to dryness. 21.03 g of the product are obtained.

Workup

  1. temperaturethe mixture is refluxed for 2 hours 30 minutes
  2. customthe solid which was formed
  3. filtrationis recovered by filtration
  4. washwashed with diethyl ether
  5. dissolutionThe solid is then dissolved in 200 ml of water
  6. additionThe mixture is added with 200 ml of ethyl acetate and it
  7. additionit is added with additional 800 ml of warm ethyl acetate
  8. customThe organic phase is separated
  9. washthe aqueous phase is washed with 200 ml of ethyl acetate
  10. washThe pooled organic phases are washed with 250 ml of saturated aqueous solution of sodium chloride
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-be7dde1df2d5486f855da6211c473c2a
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

Loading…