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Hydrochloric Acid → N-(4-t-butylphenyl)perylene-3,4-dicarboximide

HRID 266605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 266605
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=O)[C:3](=[C:4]23)[CH:2]=1)=[O:22].[C:26]([C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].N1C=CN=C1.Cl>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)C>[C:26]([C:30]1[CH:31]=[CH:32][C:33]([N:34]2[C:21](=[O:22])[C:5]3[C:4]4[C:19]5[C:8](=[CH:7][CH:6]=3)[C:9]3[C:20]6[C:13]([CH:12]=[CH:11][CH:10]=3)=[CH:14][CH:15]=[CH:16][C:17]=6[C:18]=5[CH:1]=[CH:2][C:3]=4[C:24]2=[O:23])=[CH:35][CH:36]=1)([CH3:29])([CH3:27])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 698614-Tert-ButylanilineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Produkt 1

HCID 19033222N-(4-t-butylphenyl)perylene-3,4-dicarboximideAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724192
Zinc acetate (USP)
Katalysator
HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

0.70 g (2.17 mmol) of perylene-3,4-dicarboxylic anhydride is mixed with 0.49 g (3.28 mmol) of 4-t-butylaniline, 3.00 g of imidazole and 0.10 g of zinc acetate dihydrate and the mixture is heated at 140°-150° C. for 5 h. While still hot, the mixture is treated with 100 ml of ethanol, and then 200 ml of 10% hydrochloric acid are added. The red suspension is heated until all the ethanol has evaporated, and the product is then filtered off with suction. The red-brown residue is boiled in 10% potassium carbonate solution, the solid residue is filtered off with suction while hot and rinsed several times with hot dist. water. The red residue is dried in a drying cabinet at 120° C. and then recrystallized by extraction with a toluene/methanol mixture to give 0.80 g (81%) of red N-(4-t-butylphenyl)perylene-3,4-dicarboximide which shows a red solid fluorescence. M.p. >330° C. Rf (CHCl3 /silica gel)=0.35.

Aufarbeitung

  1. temperaturethe mixture is heated at 140°-150° C. for 5 h
  2. customhas evaporated
  3. filtrationthe product is then filtered off with suction
  4. filtrationthe solid residue is filtered off with suction while hot and
  5. washrinsed several times with hot dist
  6. customThe red residue is dried in a drying cabinet at 120° C.
  7. customrecrystallized by extraction with a toluene/methanol mixture

Quellen und Nachweise

ORD-Eintrag
ord-16dd334854764a0590178515dbeeb052
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05650513

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