Potassium Carbonate → 5,11-Di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

HRID 1585961

Reaktionsgleichung

Reaktionsgleichung von HRID 1585961
[CH:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[NH:7][C:8]3[C:9](=[CH:10][C:11]4[NH:12][C:13]5[C:18]([C:19]=4[CH:20]=3)=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:2]=12.I[C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].CCCCCC[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:24]1([CH3:28])[CH:25]=[CH:26][CH:27]=[C:22]([N:12]2[C:11]3[C:19](=[CH:20][C:8]4[N:7]([C:46]5[CH:47]=[C:42]([CH3:41])[CH:43]=[CH:44][CH:45]=5)[C:3]5[C:2]([C:9]=4[CH:10]=3)=[CH:1][CH:6]=[CH:5][CH:4]=5)[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:23]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 122683-IodotolueneHCID 12388TridecaneHCID 958385,11-Dihydroindolo[3,2-b]carbazole

Produkt 1

HCID 154049595,11-Di-m-tolyl-5,11-dihydroindolo[3,2-b]carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24463Copper sulfate pentahydrateKatalysator

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

A 200 milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with 5,11-dihydroindolo[3,2-b]carbazole (5.1 grams, 0.02 mol), 3-iodotoluene (8.69 grams, 0.04 mol), copper sulfate pentahydrate (0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction mixture was heated to about 250° C. with a heating mantle and allowed to proceed at that temperature until chromatographic analysis indicated that the reaction was complete after approximately 6 hours. The heating mantle was removed and the mixture was cooled to about 100° C., and 100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase, which contains the desired product and solvent mixture, was washed with water and treated under argon with 25 grams of alumina. After the alumina was filtered off, the organic phase was evaporated to remove most of the toluene. The above product was obtained by recrystallization of the residue from cyclohexane. Yield: 6.8 grams. IR (Kbr): 1,604, 1,588, 1,490, 1,475, 1,450, 1,321, 1,201, 1,153, 760, 745, 701 cm-1. 1H-NMR (CDCl3): δ2.51 (s), 7.18-7.59 (m), 8.05 (s), 8.12 (d, J=8.5 Hz).

Aufarbeitung

  1. customA 200 milliliter 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and argon inlet
  3. customwas purged with argon
  4. customThe heating mantle was removed
  5. temperaturethe mixture was cooled to about 100° C.
  6. addition100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring
  7. customThe resulting two phase mixture was transferred into a separatory funnel
  8. customthe layers separated
  9. washwas washed with water
  10. additiontreated under argon with 25 grams of alumina
  11. filtrationAfter the alumina was filtered off
  12. customthe organic phase was evaporated
  13. customto remove most of the toluene
  14. customThe above product was obtained by recrystallization of the residue from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-06141d4b92b945838bbed33f947a8737
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942340

Verknüpfte Notizen

Wird geladen…