Malonic Acid → Mls002704122

HRID 2300038

Reaktionsgleichung

Reaktionsgleichung von HRID 2300038
[CH2:1]([NH:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](O)(=[O:24])[CH2:20][C:21](O)=[O:22].C(OC(=O)C)(=O)C>>[CH2:1]([N:8]1[C:19](=[O:24])[CH2:20][C:21](=[O:22])[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 867Malonic AcidHCID 7918Acetic AnhydrideHCID 72889Urea, N,N'-bis(phenylmethyl)-

Produkt 1

HCID 268729Mls002704122Ausbeute 95,6 %

Versuchsvorschrift

Heated was a mixture of N,N′-dibenzylurea 12.02 g (50.0 mmol) and malonic acid 5.20 g (50.0 mmol) in acetic anhydride 50.0 mL (530 mmol, 10.6 equivalents) at 70° C.-75° C. for 14 hours under a nitrogen atmosphere. Then, removed were the volatile materials under the reduced pressure and distributed the residue between layers of 2 M sodium hydroxide 250 mL and ether 200 mL. Separated was the alkaline aqueous layer and after washing with ether, neutralized with concentrated hydrochloric acid under cooling in ice-water bath (pH 2-3). Extracted was the neutrallized aqueous solution with chloroform, washed with water, and dried over sodium sulfate. Removal of the solvent under reduced pressure gave 1,3-dibenzylbarbituric acid 14.7 g as pale yellow crystalline powder (95.6% yield).

Aufarbeitung

  1. temperatureHeated
  2. customThen, removed
  3. customSeparated
  4. washafter washing with ether, neutralized with concentrated hydrochloric acid
  5. temperatureunder cooling in ice-water bath (pH 2-3)
  6. extractionExtracted
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ed18cd21528148ec8971e12a64a7d33d
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498164B1

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