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

HRID 514756ノート

反応式

HRID 514756 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-47e1f6b8566f431faffec9146346b49d
出典データセット
uspto-grants-2015_08
特許番号
US09108916B2

反応ノート

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