9-Acetyl-3-bromocarbazole → N-(9H-carbazol-3-yl)-N-(naphthalen-1-yl)-N',N'-diphenylbenzene-1,4-diamine

HRID 64534Notes

Reaction equation

HRID 64534 reaction equation
C([N:4]1[C:16]2[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=O)C.[C:18]1([NH:28][C:29]2[CH:34]=[CH:33][C:32]([N:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>[Cu]=O>[CH:6]1[C:5]2[NH:4][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[C:8]([N:28]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[C:29]2[CH:34]=[CH:33][C:32]([N:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 17148799-Acetyl-3-bromocarbazoleHCID 58811120N'-1-naphthyl-N,N-diphenyl-1,4-benzenediamine

Product 1

HCID 68088966N-(9H-carbazol-3-yl)-N-(naphthalen-1-yl)-N',N'-diphenylbenzene-1,4-diamineYield 69.6%

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Conditions

Temperature
170 °C

Procedure

A mixture of 1.2 g of 9-acetyl-3-bromocarbazole and 2.2 g of N′-1-naphthyl-N,N-diphenyl-1,4-benzenediamine were stirred together in 20 ml N,N′-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170° C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid was then taken up for further deprotection using 0.6 g KOH with TI-IF (3 ml), methanol (6 ml) and water (6 ml) at reflux temperature. The reaction mixture was then extracted using ethyl acetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene/hexane (½) as eluent, yielded 1.6 g of N-(9H-carbazol-3-yl)-N-(naphthalen-1-yl)-N′,N′-diphenylbenzene-1,4-diamine.

Workup

  1. customThe reaction was quenched with water
  2. filtrationthe solid was filtered
  3. washwashed with methanol
  4. customdried under vacuum
  5. temperatureat reflux temperature
  6. extractionThe reaction mixture was then extracted
  7. dry with materialand the organic layer was dried over anhydrous sodium sulfate
  8. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-605fa2acf83047099832614dfeb8157d
Source dataset
uspto-grants-2016_09
Patent number
US09450192B2

Reaction notes

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