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N,N,N'-triphenyl-4-phenylenediamine → HCID 59844173, Verbindung

HRID 2282792
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2282792
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=3.[C:22]1([N:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[C:49]([CH3:52])([O-])[CH3:50].[Na+]>[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:22]1([N:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:29]2[CH:34]=[CH:33][C:32]([N:35]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[C:7]5[C:12]([C:13]=4[CH:14]=3)=[CH:11][C:10]([N:35]([C:50]3[CH:49]=[CH:52][CH:41]=[CH:36][CH:37]=3)[C:32]3[CH:33]=[CH:34][C:29]([N:28]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:30][CH:31]=3)=[CH:9][CH:8]=5)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 161288N,N,N'-triphenyl-4-phenylenediamineHCID 134073473,6-Diiodo-9-phenylcarbazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 59844173HCID 59844173, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 154270
1,5-Diphenylpenta-1,4-dien-3-one;palladium
Katalysator
HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Specifically, 5.44 g (11 mmol) of 3,6-diiodo-9-phenylcarbazole, 9 g (27 mmol) of N-(4-diphenylaminophenyl)-N-phenylamine, 500 mg (0.87 mmol) of bis(dibenzylidene acetone) palladium and 3.35 mg (35 mmol) of sodium tert-butoxide were mixed in a three-neck flask. Nitrogen was substituted for air inside of the three-neck flask. Subsequently, 100 ml of dehydrated toluene was added to the mixture in the three-neck flask. The mixture added with the dehydrated toluene was degassed for about 3 minutes. Then, 4 ml of tri-tert-butyl phosphine (a 10 wt % hexane solution) was added to the mixture and then this mixture was stirred, while heating at 80° C., for 16 hours under nitrogen atmosphere. After the reaction, saturated saline was added and a product was extracted with 200 ml of ethyl acetate. Further, magnesium sulfate was added to the product to remove moisture, and then the magnesium sulfate was filtered to be removed. The filtrate was concentrated, and the concentrated filtrate was dripped in a solvent containing ethyl acetate and hexane with a ratio of 1:10 to be suspended. Afterwards, a supernatant of the suspension was collected. The supernatant was purified by a silica gel column using a solvent containing ethyl acetate and hexane with a ratio of 1:10. The resultant was concentrated to obtain a cream-colored powder. In addition, an insoluble component of the suspension was purified by a silica gel column using a solvent that contains 5:1 toluene and hexane. The resultant was concentrated to obtain a cream-colored powder. The cream-colored powders obtained in the above described manner were target matters. Specifically, 6.5 g of the cream-colored powders in total were obtained and the yield was 75%. The NMR data is shown below. The 1H-NMR (300 MHz, DMSO-d); δ=6.86-6.97 (m, 26H), 7.18-7.36 (m, 14H), 7.35 (d, j=9.0, 2H), 7.52-7.66 (m, 5H), 7.99 (s, 2H). Also, a chart of 1H-NMR is shown in FIG. 15. Also, a chart of an enlarged portion of FIG. 15 in the range of 6.0 ppm and 9.0 ppm is shown in FIG. 16.

Aufarbeitung

  1. customwas degassed for about 3 minutes
  2. additionThen, 4 ml of tri-tert-butyl phosphine (a 10 wt % hexane solution) was added to the mixture
  3. customAfter the reaction, saturated saline
  4. additionwas added
  5. extractiona product was extracted with 200 ml of ethyl acetate
  6. additionFurther, magnesium sulfate was added to the product
  7. customto remove moisture
  8. filtrationthe magnesium sulfate was filtered
  9. customto be removed
  10. concentrationThe filtrate was concentrated
  11. additioncontaining ethyl acetate and hexane with a ratio of 1:10
  12. customAfterwards, a supernatant of the suspension was collected
  13. customThe supernatant was purified by a silica gel column
  14. additioncontaining ethyl acetate and hexane with a ratio of 1:10
  15. concentrationThe resultant was concentrated
  16. customto obtain a cream-colored powder
  17. customIn addition, an insoluble component of the suspension was purified by a silica gel column
  18. concentrationThe resultant was concentrated
  19. customto obtain a cream-colored powder
  20. customThe cream-colored powders obtained in the

Quellen und Nachweise

ORD-Eintrag
ord-1833b61d851749569a6fa8801af2f2bd
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09142783B2

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