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2-Methoxyethanol → [11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]-carbazole-8-yl}-[2-(2-methoxyethoxy)phenyl]-methanone oxime

HRID 2172360
ノート
印刷プレビュー

反応式

HRID 2172360 の反応式
[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])=[O:23])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1F)[CH:10]=2)[CH3:2].[CH3:46][O:47][CH2:48][CH2:49][OH:50].CC(C)([O-])C.[K+].[Cl-].[OH:58][NH3+:59]>N1C=CC=CC=1.O>[CH2:1]([CH:3]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:23])[C:24]3[C:25]([CH3:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=3[CH3:30])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:33]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:50][CH2:49][CH2:48][O:47][CH3:46])=[N:59][OH:58])[CH:10]=2)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 80192-MethoxyethanolHCID 21645Hydroxylamine HClHCID 23665647Potassium tert-butoxideHCID 6809414611-(2-Ethylhexyl)-8-(2-fluorobenzoyl)-11H-benzo[a]carbazole-5-yl-(2,4,6-trimethylphenyl)-methanone

生成物 1

HCID 131732959[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]-carbazole-8-yl}-[2-(2-methoxyethoxy)phenyl]-methanone oxime収率 71%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

To 11-(2-Ethylhexyl)-8-(2-fluorobenzoyl)-11H-benzo[a]carbazole-5-yl-(2,4,6-trimethylphenyl)-methanone (5.98 g; 10.0 mmol) in pyridine (10 mL) are added 2-methoxyethanol (2.28 g; 30.00 mmol) and potassium tert-butoxide (1.68 g; 15.00 mmol) at room temperature. The mixture is heated at 80° C., and it is stirred for 3.5 hours. To the reaction mixture is added hydroxylammonium chloride (2.08 g; 30.00 mmol), and then the mixture is stirred at 100° C. overnight. After it is cooled at room temperature, the reaction mixture is poured into 200 ml of water. The precipitated solid is collected by filtration, and then it is washed with CH3OH. The desired compound is obtained in 71% yield (4.73 g) as a white solid. The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.81 (t), 0.87 (t), 1.17-1.43 (m), 2.18 (s), 2.26-2.28 (m), 2.36 (s), 2.39 (s), 2.96 (s), 3.08 (t), 3.11 (t), 3.45 (t), 3.81 (t), 4.08 (t), 4.65-4.75 (m), 6.87 (d), 6.93 (s), 7.03-7.12 (m), 7.24-7.26 (m), 7.36-7.47 (m), 7.50-7.51 (m), 7.57 (br), 7.67-7.76 (m), 8.27 (d), 8.30 (d), 8.33 (s), 8.62 (d), 9.55 (dd), 9.59 (dd)

後処理

  1. stirringthe mixture is stirred at 100° C. overnight
  2. temperatureAfter it is cooled at room temperature
  3. filtrationThe precipitated solid is collected by filtration
  4. washit is washed with CH3OH

出典と根拠

ORDレコード
ord-49aca51e5ffe43448c616739a000c8f9
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051397B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート