Imidazole → Perylene

HRID 266597

Reaktionsgleichung

Reaktionsgleichung von HRID 266597
[CH:1]1[C:10]2[C:11]3[CH:20]=[CH:19][C:18]4C(OC(=O)[C:16]5[C:17]=4[C:12]=3[C:13](=[CH:14][CH:15]=5)[C:8]3[C:9]=2[C:4]2[C:5](C(OC(=O)[C:3]=2[CH:2]=1)=O)=[CH:6][CH:7]=3)=O.N1C=CN=C1.O.C(C1C=CC(C(C)(C)C)=CC=1N)(C)(C)C>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH:14]1[C:13]2=[C:12]3[C:11]([C:10]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][C:8]2=5)[CH:3]=[CH:2][CH:1]=4)=[CH:20][CH:19]=[CH:18][C:17]3=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 671913,4,9,10-Perylenetetracarboxylic dianhydrideHCID 6054882,5-di-tert-Butylaniline

Produkt 1

HCID 9142Perylene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724192Zinc acetate (USP)Katalysator

Reaktionsbedingungen

Temperatur
210 °C

Versuchsvorschrift

In an autoclave of capacity 100 ml, a mixture of 3.66 g (9.34 mmol) of perylene-3,4,9,10-tetracarboxylic dianhydride, 18.7 g of imidazole, 1.32 g of zinc acetate dihydrate, 8.0 ml (450 mmol) of water and 1.05 g (5.12 mmol) of 2,5-di-tert-butylaniline (prepared according to Rec. Trav. Chim. Pays-Bas, 1958, 77, 491) is heated at 210° C. for 23 h. After the end of the reaction, the mixture is removed from the autoclave by rinsing with ethanol, treated with water and concentrated hydrochloric acid and boiled until all the ethanol has evaporated. The brown-red residue is filtered off with suction and boiled in 10 per cent potassium carbonate solution for 1 h. The residue is filtered off with suction, dried at 120° C. in a drying cabinet and chromatographed on silica gel using chloroform. This gives a forerun (yellow, blue fluorescence) of perylene, followed by N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide (2b) and then by N,N'-bis(2,5-di-tert-butylphenyl)perylene-3,4,9,10-tetracarboximide (1b). Yield 2.40 g (50.5%), m.p. >300° C. Rf (CHCl3 /silica gel)=0.85. UV (CHCl3): λmax (ε)=489 nm (35300), 512 (33590). Fluorescence (CHCl3,exc. 489 nm) λmax (Irel)=535 nm (1), 576 nm (0.36).

Aufarbeitung

  1. customAfter the end of the reaction
  2. customthe mixture is removed from the autoclave
  3. washby rinsing with ethanol
  4. additiontreated with water and concentrated hydrochloric acid
  5. customhas evaporated
  6. filtrationThe brown-red residue is filtered off with suction
  7. filtrationThe residue is filtered off with suction
  8. customdried at 120° C. in a drying cabinet
  9. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eac0cead600140f88fe11665d85153d0
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650513

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