Benzaldehyde → 1,3-Dimethyl-5-nitro-6-styryluracil

HRID 1784358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784358
[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1CCCCC1>C(O)C>[CH3:1][N:2]1[C:7](/[CH:8]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([N+:9]([O-:11])=[O:10])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 7503695-Nitro-1,3,6-trimethyluracil

Produkt 1

HCID 53656311,3-Dimethyl-5-nitro-6-styryluracilAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1,3,6-trimethyl-5-nitro-1H-pyrimidine-2,4dione (3.00 g, 15.06 mmol), benzaldehyde (1.58 ml, 15.56 mmol), piperidine (1.41 ml, 15.56 mmol) and a 3 Å molecular sieve (6.00 g) in ethanol (70 ml) was refluxed for 4 hours, filtered and the solid was treated with a mixture of chloroform and methanol. The resulting suspension was filtered again and the filtrates were evaporated. The residue was triturated with diethyl ether and the precipitate collected by filtration and dried under vacuum to yield 1,3-dimethyl-5-nitro-6-((E)styryl)-1H-pyrimidine-2,4-dione (2.61 g, 60%) as a yellow solid.

Aufarbeitung

  1. filtrationfiltered
  2. additionthe solid was treated with a mixture of chloroform and methanol
  3. filtrationThe resulting suspension was filtered again
  4. customthe filtrates were evaporated
  5. customThe residue was triturated with diethyl ether
  6. filtrationthe precipitate collected by filtration
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8f03aa728ca143b69b12629aa0cc946b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504398B2

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