Benzylurea → 3,5-dibenzylpyrimidine-2,4,6(1H,3H)-trione

HRID 357114

Reaktionsgleichung

Reaktionsgleichung von HRID 357114
[CH2:1]([NH:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[O-].[Na+]>CO>[CH2:1]([N:8]1[C:25](=[O:26])[CH:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:20](=[O:21])[NH:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10853BenzylureaHCID 69090Diethyl 2-benzylpropanedioateHCID 10942334Sodium Methoxide

Produkt 1

HCID 2687313,5-dibenzylpyrimidine-2,4,6(1H,3H)-trione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 22.53 g (150 mmol) of benzylurea and 37.5 g (150 mmol) of diethyl benzylmalonate in 77 ml of methanol, 36.6 ml (150 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 48.35 g (quant., white crystal) of the desired product.

Aufarbeitung

  1. additionwas added at room temperature
  2. temperatureby refluxing for 16 hours
  3. temperatureAfter the reaction mixture was cooled
  4. distillationthe solvent was distilled off
  5. dissolutionAfter the residue was dissolved in water
  6. filtrationinsoluble substances were filtered out
  7. additionby adding concentrated hydrochloric acid
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water and n-hexane-diethyl ether
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fc41fb9c6da048e2b5254e8a37fbde92
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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