Carbazole, 9-(3-(dimethylamino)propyl)- → 1,1'-{9-[3-(Dimethylamino)propyl]-9H-carbazole-3,6-diyl}bis(2-methylpropan-1-one)

HRID 1615003노트

반응식

HRID 1615003 반응식
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:12]1[C:11]2[CH:10]=[CH:9][C:8]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[C:3]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH:4]=2

참가 물질

5

반응물 3

HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 453806051,1'-{9-[3-(Dimethylamino)propyl]-9H-carbazole-3,6-diyl}bis(2-methylpropan-1-one)수율 48.1%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

실험 절차

Compound 30 (0.25 g, 1.0 mmol) was dissolved in nitrobenzene (5 mL). AlCl3 (0.6 g, 4.5 mmol) and then isobutyroyl chloride (0.6 mL, 5.7 mmol) were added in portions. The reaction mixture was stirred for 40 min (LC/MS monitoring). The obtained mixture was poured into ice/water mixture and extracted with CHCl3. The combined extracts were evaporated, and the residue was purified by chromatography in a short thick silica gel column (eluent: CHCl3/MeOH 99:1→90:10) to afford 0.189 g (47%) of the product. 1H NMR (DMSO-d6): δ 1.20 (12H, d, J=6.7 Hz); 1.90-1.97 (2H, m); 2.11 (6H, s); 2.18 (2H, t, J=6.7 Hz); 3.91 (2H, septet, J=6.7 Hz), 4.50 (2H, t, J=6.6 Hz); 7.76 (2H, d, J=8.7 Hz); 8.14 (2H, dd, J=8.7 Hz, J=1.5 Hz); 9.11 (2H, d, J=1.5 Hz). ELSD: 100%, ESI-MS: m/z 392 [M+H]+.

후처리

  1. extractionextracted with CHCl3
  2. customThe combined extracts were evaporated
  3. customthe residue was purified by chromatography in a short thick silica gel column (eluent: CHCl3/MeOH 99:1→90:10)

출처 및 근거

ORD 기록
ord-b36b3abb625f4ba9a6783fb6cadf12a9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765738B2

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