Triphenylphosphine → 11-Bromoundecylmaleimide pentacene

HRID 500287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500287
[CH:1]1[C:22]2[C:5](=[CH:6][C:7]3[C:20]([CH:21]=2)=[CH:19][C:18]2[C:9](=[CH:10][C:11]4[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[C:23]1(=[O:29])[NH:27][C:26](=[O:28])[CH:25]=[CH:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][C:24]1[C:23]([NH:27][C:26](=[O:28])[CH:25]=1)=[O:29].[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1.[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][N:27]1[C:26](=[O:28])[CH:25]=[CH:24][C:23]1=[O:29].[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 7416311-Bromo-1-undecanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86643198Pentacene maleimide

Produkt 2

HCID 8664775211-Bromoundecylmaleimide pentaceneHCID 86647754N-(11-bromoundecyl) maleimide pentacene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Pentacene-maleimide adduct (5c) (375 mg, 1 mmole) are added to a solution of triphenyl phosphine (393 mg, 1.5 mmole) and 11-bromo-1-undecanol (375 mg, 1.5 mmole) in 40 mL of anhydrous tetrahydrofuran. To this mixture a solution of diisopropyl azodicarboxylate (300 mg, 1.5 mmole) in 10 mL of anhydrous THF is added dropwise under a stream of nitrogen. After completion of the addition, the solution is stirred at room temperature for 18 hours. The solvent is evaporated under reduced pressure and the residue is titrated with diethyl ether and the precipitate is filtered, washed with 1:1 ether-hexane and dried. Crystallization from benzene affords the pure sample of 11-bromoundecylmaleimide-pentacene adduct 5d.

Aufarbeitung

  1. additionAfter completion of the addition
  2. customThe solvent is evaporated under reduced pressure
  3. filtrationthe precipitate is filtered
  4. washwashed with 1:1 ether-hexane
  5. customdried
  6. customCrystallization from benzene

Quellen und Nachweise

ORD-Eintrag
ord-8ca79133d16f4ad49136e6255d18ca23
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07771695B2

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