Dicyclohexylcarbodiimide → 2,3-Dicyano-4-octyloxyphenyl 5-dodecylthiophene-2-carboxylate

HRID 892388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892388
[CH2:1]([C:13]1[S:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:21]([O:29][C:30]1[CH:36]=[CH:35][C:33](O)=[C:32]([C:37]#[N:38])[C:31]=1[C:39]#[N:40])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CC=CN=2)CCCC1>C1COCC1>[CH2:1]([C:13]1[S:17][C:16]([C:18]([O:20][C:33]2[CH:35]=[CH:36][C:30]([O:29][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:31]([C:39]#[N:40])[C:32]=2[C:37]#[N:38])=[O:19])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 110190202-(Pyrrolidin-1-yl)pyridineHCID 149850905-Dodecylthiophene-2-carboxylic acidHCID 189953942,3-Dicyano-4-octyloxyphenol

Produkt 1

HCID 150066912,3-Dicyano-4-octyloxyphenyl 5-dodecylthiophene-2-carboxylateAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.50 g (1.69 mM) of 5-dodecylthiophene-2-carboxylic acid (M.W.: 296), 0.46 g (1.69 mM) of 2,3-dicyanohydroquinone monooctyl ether (M.W.: 272) and 20 ml of THF were mixed and stirred. To the mixture, 0.35 g (1.69 mM) of dicyclohexylcarbodiimide (M.W.: 206) and 0.05 g of pyrrolidinopyridine were added, followed by stirring overnight at room temperature. After the reaction, the reaction mixture was subjected to filtration and the filtrate was subjected to distillation to obtain a crude product. The crude product was purified by silica gel column chromatography with the use of benzene and recrystallized from ethanol to obtain 0.54 g of an objective product (yield: 58.1%).

Aufarbeitung

  1. stirringby stirring overnight at room temperature
  2. customAfter the reaction
  3. filtrationthe reaction mixture was subjected to filtration
  4. distillationthe filtrate was subjected to distillation
  5. customto obtain a crude product
  6. customThe crude product was purified by silica gel column chromatography with the use of benzene
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ed5edfed4f1840f29c305b40913f293d
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118441

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