(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester → (E)-5,5-bis(4-methoxyphenyl)-N-[1,1-dimethyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide

HRID 1110541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110541
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=CC=1)([O-])=O.[CH3:33][C:34]([CH3:45])([NH2:44])[CH2:35][CH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1>O1CCCC1>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:44][C:34]([CH3:45])([CH3:33])[CH2:35][CH2:36][CH2:37][C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)=[O:10])=[CH:29][CH:28]=1

Komponenten

4

Edukt 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 14547286alpha,alpha-Dimethyl-3-pyridinebutanamine

Produkt 1

HCID 14347338(E)-5,5-bis(4-methoxyphenyl)-N-[1,1-dimethyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

As in Example 134, a solution of (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.73 g) and alpha,alpha-dimethyl-3-pyridinebutanamine (0.9 mL) in tetrahydrofuran (20 mL) was stirred for 20 hours at room temperature and then at reflux for an additional 24 hours to complete the reaction. After the usual work up, the crude amide was crystallized from ethyl acetate-hexane (2x) to furnish 1.55 g of (E)-5,5-bis(4-methoxyphenyl)-N-[1,1-dimethyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 144°-145° C. Anal. Calculated for C30H34N2O3 : C, 76.57; H, 7.28; N, 5.95 Found: C, 76.70; H, 7.48; N, 6.20.

Aufarbeitung

  1. temperatureat reflux for an additional 24 hours
  2. customthe reaction
  3. customAfter the usual work up, the crude amide was crystallized from ethyl acetate-hexane (2x)

Quellen und Nachweise

ORD-Eintrag
ord-f2302d792bb04638a517e27fdcac6908
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04975438

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