Methyl acetoacetate → Dimethyl 4-[2(4-bromobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4658

Reaktionsgleichung

Reaktionsgleichung von HRID 4658
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:8]=1[CH:9]=O.[C:19]([O:25][CH3:26])(=[O:24])[CH2:20][C:21]([CH3:23])=O.[CH3:27][O:28][C:29](=[O:34])/[CH:30]=[C:31](\[NH2:33])/[CH3:32]>C(O)(C)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:8]=1[CH:9]1[C:20]([C:19]([O:25][CH3:26])=[O:24])=[C:21]([CH3:23])[NH:33][C:31]([CH3:32])=[C:30]1[C:29]([O:28][CH3:27])=[O:34]

Komponenten

5

Edukt 3

HCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 140504912-(4-Bromobutoxy)-5-methylsulfonylbenzaldehyde

Produkt 1

HCID 14050492Dimethyl 4-[2(4-bromobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

7.6 g of 2-(4-bromobutoxy)-5-methylsulfonylbenzaldehyde, 2.6 g of methyl acetoacetate and 2.9 g of 3-aminocrotonic acid methyl ester were dissolved in 16 ml of isopropanol, and the solution was heated for 5 hours. After cooling, precipitated crystals were collected by filtration, and recrystallized from methanol to give 6.3 g of dimethyl 4-[2(4-bromobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Aufarbeitung

  1. temperaturethe solution was heated for 5 hours
  2. temperatureAfter cooling
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-345b767ded454aba98cfa55ad8b0d94c
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727082

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