2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → 1,4-Dihydro-2,6-dimethyl-4-(2-methylbenzo[b]thien-3-yl)-3,5-pyridinedicarboxylic acid, diethyl ester

HRID 542774

Reaktionsgleichung

Reaktionsgleichung von HRID 542774
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[CH:11]=O.[NH2:13]/[C:14](/[CH3:21])=[CH:15]\[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH3:21][C:14]1[NH:13][C:14]([CH3:21])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]([C:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

4

Edukt 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-2×HCID 37754672-Methyl-1-benzothiophene-3-carbaldehyde

Produkt 1

HCID 138268541,4-Dihydro-2,6-dimethyl-4-(2-methylbenzo[b]thien-3-yl)-3,5-pyridinedicarboxylic acid, diethyl esterAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2.2 g of 2-methylbenzo[b]thiophene-3-carboxaldehyde, 4.9 g of ethyl 3-aminocrotonate, and 10 ml of ethanol were heated to reflux for approximately 18 hours. An additional 1.6 g of ethyl 3-aminocrotonate were added and the reaction was heated an additional 24 hours at reflux. The reaction mixture was cooled and concentrated and the resulting solid was recovered by filtration providing 2.15 g of the desired title product, m.p. 191°-193° C.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureto reflux for approximately 18 hours
  3. temperaturethe reaction was heated an additional 24 hours
  4. temperatureat reflux
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated
  7. filtrationthe resulting solid was recovered by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1d3dcd6e82f24cff84d6d8aa644653d9
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659717

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