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Urea → 5-(1-Methylethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1643354
Notes
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Reaction equation

HRID 1643354 reaction equation
[Na].[C:2]([O:10]CC)(=O)[CH2:3][C:4]([O:6]CC)=O.Br[CH:14]([CH3:16])[CH3:15].[NH2:17][C:18]([NH2:20])=[O:19]>C(O)C.CO.O.Cl>[CH:14]([CH:3]1[C:2](=[O:10])[NH:20][C:18](=[O:19])[NH:17][C:4]1=[O:6])([CH3:16])[CH3:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 1176UreaHCID 63582-BromopropaneHCID 7761Diethyl MalonateHCID 5360545Sodium2×

Product 1

HCID 818745-(1-Methylethyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneYield 43.4%

Reagents, catalysts & solvents 4

HCID 313
Hydrochloric Acid
Solvent
HCID 702EthanolSolvent
HCID 887MethanolSolvent
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium metal (1.28 kg, 55.65 mol) was dissolved in ethanol (25 L) under nitrogen atmosphere at 0° C. (bath temperature). Diethyl malonate (7.45 kg, 46.51 mol) was added to the solution and the mixture was heated to 80° C. 2-Bromopropane (8.00 kg, 65 mol) was added dropwise to the solution for 1 hour, and the solution was refluxed for 10 hours. The solution was cooled to room temperature. Sodium metal (1.22 kg, 53.04 mol) was dissolved into the solution under nitrogen atmosphere at 0° C. Urea (2.78 kg, 46.28 mol) in methanol (15 L) was added to the solution over 2 hours and the reaction mixture was refluxed for 20 hours. The reaction mixture was diluted with water (35 L) and conc. HCl (5 L), and cooled to room temperature. The precipitate was collected by filtration, washed with water (20 L), ether (15 L), n-hexane (20 L) and dried in vacuum at 40° C. for 10 hours to give 5-isopropylbarbituric acid as a white solid (3.42 kg, 20.10 mol, 43% yield).

Workup

  1. temperaturethe solution was refluxed for 10 hours
  2. temperatureThe solution was cooled to room temperature
  3. temperaturethe reaction mixture was refluxed for 20 hours
  4. temperaturecooled to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (20 L), ether (15 L), n-hexane (20 L)
  7. customdried in vacuum at 40° C. for 10 hours

Sources & evidence

ORD record
ord-c6053edb77fd44cabe31e4607f917f38
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08119800B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes