Malonic Acid → HCID 19987102, compound

HRID 973910Notes

Reaction equation

HRID 973910 reaction equation
[CH2:1]([CH:3]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][NH:5][C:6]([NH2:8])=[O:7])[CH3:2].[C:13](O)(=[O:18])[CH2:14][C:15](O)=[O:16]>C(O)(=O)C>[CH2:1]([CH:3]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][N:5]1[C:13](=[O:18])[CH2:14][C:15](=[O:16])[NH:8][C:6]1=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 533894HCID 533894, compound

Product 1

HCID 19987102HCID 19987102, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 500 g of N-(2-ethylhexyl)urea and 36 g of malonic acid in 100 ml of acetic acid was heated at 80° C. and stirred for 4 hours. After allowing to cool, the acetic acid was removed under reduced pressure and extracted by adding 100 ml of water and 500 ml of chloroform. The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and then washed with a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate. The chloroform was distilled off under reduced pressure, the residue was washed with n-hexane and collected by filtration to obtain 64 g of N-(2-ethylhexyl)barbituric acid.

Workup

  1. temperatureto cool
  2. customthe acetic acid was removed under reduced pressure
  3. extractionextracted
  4. additionby adding 100 ml of water and 500 ml of chloroform
  5. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationThe chloroform was distilled off under reduced pressure
  9. washthe residue was washed with n-hexane
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-87c3083b923d4420872a3a2c49b3a29c
Source dataset
uspto-grants-1991_11
Patent number
US05066573

Reaction notes

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