Piperidine → 6-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione

HRID 496310

Reaktionsgleichung

Reaktionsgleichung von HRID 496310
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[N:4]([CH2:13][CH2:14][CH3:15])[C:3]1=[O:16].[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)[CH3:18].N1CCCCC1>C(O)C>[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1/[CH:22]=[CH:12]/[C:5]1[N:4]([CH2:13][CH2:14][CH3:15])[C:3](=[O:16])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=1[N+:9]([O-:11])=[O:10])[CH3:18]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 11950Benzaldehyde, 2-ethoxy-HCID 223255723,6-dimethyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione

Produkt 1

HCID 223255706-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dioneAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3,6-dimethyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione (6.25 g, 27.5 mmol), 2-ethoxybenzaldehyde (4.24 mL, 30.3 mmol), piperidine (2.83 mL, 28.6 mmol) and 3 Å molecular sieves (8.75 g) in ethanol (125 mL) was refluxed for 5 hours. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure. The residue was triturated with isopropyl ether and the precipitate collected by filtration and dried under vacuum to yield 6-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione (7.42 g, 75%) as a yellow solid.

Aufarbeitung

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated with isopropyl ether
  5. filtrationthe precipitate collected by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ded9ff69bbb7454797577c9f12b2c426
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943253B2

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