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Phenylacetyl chloride → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone

HRID 2172364
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HRID 2172364 반응식
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:22][C:23]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:24]=1[C:25](Cl)=[O:26].[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:17]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][N:8]1[C:7]2[C:15](=[CH:16][C:17]([C:25](=[O:26])[C:24]3[C:23]([CH3:22])=[CH:31][C:30]([CH3:32])=[CH:29][C:28]=3[CH3:33])=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([C:41](=[O:42])[CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:13]=2)[CH3:16]
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참가 물질

6

반응물 4

HCID 7679Phenylacetyl chlorideHCID 9196Benzo[a]carbazoleHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2회

생성물 1

HCID 866905311-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone수율 159.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To 11H-benzo[a]carbazole (1.06 g, 3.23 mmol) in CH2Cl2 (5 ml) are added AlCl3 (0.510 g, 3.82 mmol) and 2,4,6-trimethylbenzoyl chloride (0.59 g, 3.24 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.51 g, 3.82 mmol) and phenylacetyl chloride (0.52 g, 3.39 mmol) are added at 0° C. The reaction mixture is stirred at room temperature for 2 hours, and then it is poured into ice-water. The crude product is extracted with CH2Cl2, and washed with water and brine. After drying over MgSO4 and concentration, the product is reprecipitated from CH2Cl2 and n-hexane to obtain a white powder (1.53 g, 81%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.79-0.91 (m), 1.18-1.50 (m), 2.19 (s), 2.28 (m), 2.41 (s), 4.38 (s), 4.74 (m), 6.97 (s), 7.22-7.36 (m), 7.56 (d), 7.71 (t), 7.77 (t), 8.14 (d), 8.35 (s), 8.62 (d), 8.63 (s), 9.58 (s).

후처리

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. extractionThe crude product is extracted with CH2Cl2
  3. washwashed with water and brine
  4. dry with materialAfter drying over MgSO4 and concentration
  5. customthe product is reprecipitated from CH2Cl2 and n-hexane

출처 및 근거

ORD 기록
ord-2708f94ef57847c0879d48675562135a
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051397B2

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