Cesium carbonate → 9,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthracene

HRID 1172782노트

반응식

HRID 1172782 반응식
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:36]1([C:42]2[NH:46][C:45]3[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=3[N:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1C2C(=CC=C3C=2N=NC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu](I)I>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[C:5]1[C:4]2[C:13]([C:12]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[C:11]3[C:6]=1[CH:7]=[C:8]([N:46]1[C:45]4[CH:47]=[CH:48][CH:49]=[CH:50][C:44]=4[N:43]=[C:42]1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:9]=[CH:10]3)=[CH:14][CH:15]=[CH:2][CH:3]=2

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 128552-PhenylbenzimidazoleHCID 601987Benzo[h]cinnolineHCID 222471572-Bromo-9,10-di(naphthalen-2-yl)anthracene

생성물 1

HCID 231602259,10-di(2-naphthyl)-2-(2-phenyl-1H-benzimidazol-1-yl)anthracene수율 35.3%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

실험 절차

5.1 g (10 mmol) of 2-bromo-9,10-di(2-naphthyl)anthracene, 2.3 g (12 mmol) of 2-phenyl-1H-benzimidazole, 0.19 g (11.0 mmol) of copper iodide, and 3.6 g (2.0 mmol) of 9,10-phenanthroline were dissolved into a 2 M solution of cesium carbonate in dimethylformamide (DMF), and the whole was refluxed under heating for 48 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered. The filtrate was poured into 1 L of 10-mass % hydrochloric acid, and the whole was extracted with methylene chloride. An organic layer was taken out and dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resultant solid was purified by means of silica gel column chromatography to obtain 2.2 g of a pale yellow solid (35% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 622 with respect to a molecular weight of 622.24.

후처리

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 48 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. additionThe filtrate was poured into 1 L of 10-mass % hydrochloric acid
  6. extractionthe whole was extracted with methylene chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant solid was purified by means of silica gel column chromatography

출처 및 근거

ORD 기록
ord-b14732359192416fbddfeac0cfd11b95
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833632B2

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