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Ethyl Bromide → Ethyl 4-[N-ethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

HRID 1097395
ノート
印刷プレビュー

反応式

HRID 1097395 の反応式
[H-].[Na+].[CH3:3][C:4]12[C:16]3[C:8](=[CH:9][C:10]([NH:17][C:18]4[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=4)=[CH:11][C:12]=3[CH2:13][CH2:14][CH2:15]1)[CH2:7][CH2:6][CH2:5]2.Br[CH2:30][CH3:31].[Cl-].[NH4+]>CN(C)C=O>[CH2:30]([N:17]([C:10]1[CH:9]=[C:8]2[C:16]3[C:4]([CH3:3])([CH2:5][CH2:6][CH2:7]2)[CH2:15][CH2:14][CH2:13][C:12]=3[CH:11]=1)[C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][CH:28]=1)[CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 25190221Ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

生成物 1

HCID 58526562Ethyl 4-[N-ethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate収率 98%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

A suspension of sodium hydride (60%, 0.013 g) in N,N-dimethylformamide (3 ml) was added with ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.055 g) dissolved in N,N-dimethylformamide (2 ml), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with bromoethane (0.025 ml), the mixture was stirred overnight at room temperature, and then added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to obtain the title compound (0.058 g, yield: 98%).

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50)

出典と根拠

ORDレコード
ord-c784e902999e41899198d75946dcf8cb
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08143260B2

反応ノート

読み込み中…

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