(3-Trifluoromethylphenyl)urea → Allyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 1798843

Reaktionsgleichung

Reaktionsgleichung von HRID 1798843
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16].[C:25]([O:31][CH2:32][CH:33]=[CH2:34])(=[O:30])[CH2:26][C:27]([CH3:29])=O>O1CCOCC1>[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]2[C:26]([C:25]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])=[C:27]([CH3:29])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=3)[C:10](=[O:11])[NH:12]2)=[CH:19][CH:18]=1)#[N:16]

Komponenten

5

Edukt 3

HCID 25712(3-Trifluoromethylphenyl)ureaHCID 660424-CyanobenzaldehydeHCID 70701Allyl acetoacetate

Produkt 1

HCID 59684802Allyl 4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

45.0 g ethyl polyphosphate are dissolved in 150 ml dioxane, 15.0 g (73.5 mmol) N-[3-(trifluoro-methyl)phenyl]urea, 19.3 g (147 mmol) 4-cyanobenzaldehyde and 20.9 g (147 mmol) allyl acetoacetate are added, and the mixture is stirred under reflux overnight. Volatiles are evaporated in vacuo, the remainder is dissolved in ethyl acetate and sequentially washed with saturated sodium hydrogencarbonate, sodium hydrogensulfite and sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The crude product is purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate).

Aufarbeitung

  1. temperatureunder reflux overnight
  2. customVolatiles are evaporated in vacuo
  3. dissolutionthe remainder is dissolved in ethyl acetate
  4. washsequentially washed with saturated sodium hydrogencarbonate, sodium hydrogensulfite and sodium chloride solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe crude product is purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6117047167004337af8f329ef4c43977
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343987B2

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