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

HRID 64534노트

반응식

HRID 64534 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 14829Copper oxide촉매

반응 조건

온도
170 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-605fa2acf83047099832614dfeb8157d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09450192B2

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