Urea → HCID 18408262, compound

HRID 992842Notes

Reaction equation

HRID 992842 reaction equation
[Na].[NH2:2][C:3]([NH2:5])=[O:4].[CH:6]1([CH:11]([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7]1>C(O)C>[CH:6]1([CH:11]2[C:12](=[O:13])[NH:5][C:3](=[O:4])[NH:2][C:17]2=[O:18])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 1176UreaHCID 2492691,3-Diethyl 2-cyclopentylpropanedioateHCID 5360545Sodium

Product 1

HCID 18408262HCID 18408262, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3.48 g (151 mmol) of sodium in 50 mL absolute ethanol was added 3.02 g (50 mmol) urea and 10 g (44 mmol) of the diethyl cyclopentylmalonate prepared above. The thick white slurry which formed was refluxed for 12 hours. Most of the ethanol was removed via rotary evaporation, and the residue was diluted with 100 mL of water and acidified with 10 mL of 98% H2SO4. The resulting white solid which formed was collected by filtration and dried on a pump. The solid was recrystallized from water, and recrystallized a second time from 5% water/ethanol to obtain 7.006 g of colorless platelike crystals with a melting point of 222-223° C.

Workup

  1. customprepared above
  2. customThe thick white slurry which formed
  3. temperaturewas refluxed for 12 hours
  4. customMost of the ethanol was removed via rotary evaporation
  5. additionthe residue was diluted with 100 mL of water
  6. customThe resulting white solid which formed
  7. filtrationwas collected by filtration
  8. customdried on a pump
  9. customThe solid was recrystallized from water
  10. customrecrystallized a second time from 5% water/ethanol
  11. customto obtain 7.006 g of colorless platelike crystals with a melting point of 222-223° C.

Sources & evidence

ORD record
ord-7bc86c6fe7dc49c39bd6f6838a22d593
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

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