Dimethylformamide → 9,3':6',9''-Ter-9H-carbazole

HRID 1784328Notes

Reaction equation

HRID 1784328 reaction equation
C([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([N:21]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:22]3=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([N:34]1[C:46]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[C:40]3[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:13]=2)C1C=CC=CC=1.C(=NC1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].CN(C=O)C>O>[CH:45]1[C:46]2[N:34]([C:12]3[CH:11]=[CH:10][C:9]4[NH:8][C:20]5[C:15]([C:14]=4[CH:13]=3)=[CH:16][C:17]([N:21]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:27]4[C:22]3=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:18][CH:19]=5)[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:41]=2[CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10858N-BenzylideneanilineHCID 23665647Potassium tert-butoxideHCID 68880940N-benzyl-3,6-di(N-carbazolyl)carbazole

Product 1

HCID 121038909,3':6',9''-Ter-9H-carbazoleYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Under a nitrogen atmosphere, a suspension of N-benzyl-3,6-di(N-carbazolyl)carbazole (2.06 g, 3.5 mmol), benzylideneaniline (1.27 g, 7.0 mmol) and t-BuOK (5.06 g, 50 mmol) in a dried DMF (30 mL) was stirred at 75° C. for 4 hours. Water (about 150 mL) was added and black tar precipitated was filtrated. The tar-like material was dissolved in hot chloroform, to which anhydrous magnesium sulfate and activated carbon were added to be stirred for 30 minutes with heating. The mixture was filtrated, the filtrated liquid was concentrated, and then the residuum was recrystallized with chloroform/ethanol to give the compound in the title, (3,6-di(N-carbazolyl)carbazole) as beige powder. The yield was 29%. The melting point was 185 to 187° C. NMR data are shown in FIG. 17 (1H NMR) and FIG. 18 (13C NMR).

Workup

  1. customblack tar precipitated
  2. filtrationwas filtrated
  3. dissolutionThe tar-like material was dissolved in hot chloroform, to which anhydrous magnesium sulfate and activated carbon
  4. additionwere added
  5. stirringto be stirred for 30 minutes
  6. temperaturewith heating
  7. filtrationThe mixture was filtrated
  8. concentrationthe filtrated liquid was concentrated
  9. customthe residuum was recrystallized with chloroform/ethanol

Sources & evidence

ORD record
ord-ccd31ce8c37c4c539d85f1eb1d376fda
Source dataset
uspto-grants-2009_03
Patent number
US07504162B2

Reaction notes

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