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Potassium Iodide → (1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone

HRID 220783
ノート
印刷プレビュー

反応式

HRID 220783 の反応式
[H-].[Na+].[C:3]([N:11]1[CH2:20][CH2:19][C:18]2[N:17]=[C:16]([CH3:21])[NH:15][C:14]=2[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]1=2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[I-].[K+]>C1COCC1>[CH2:26]([N:15]1[C:14]2[C:13]3[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=3[N:11]([C:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[O:10])[CH2:20][CH2:19][C:18]=2[N:17]=[C:16]1[CH3:21])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
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

6

反応物 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178432322HCID 178432322、化合物

生成物 1

HCID 57555380(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-phenyl-methanone収率 90.4%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (60% dispersion in oil, 905 mg, 22.5 mmol) was placed in anhydrous THF (200 ml) and cooled down to 0° C. 6-Benzoyl-2-methyl-1,4,5,6-tetrahydro-1,3,6-triaza-benzo[e]azulene from Example E5.8 (4.9 g, 16.1 mmol) was added dropwise and the mixture was stirred for 1 h at room temperature. Benzyl bromide (2.31 ml, 19.3 mmol) and potassium iodide (1.34 g, 8.0 mmol) were added and the mixture was stirred for 16 h. The solution was diluted with EtOAC, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc) to yield the title compound (5.73 g, 90%).

後処理

  1. stirringthe mixture was stirred for 16 h
  2. additionThe solution was diluted with EtOAC
  3. washwashed with saturated NaHCO3
  4. dry with materialbrine, dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; EtOAc)

出典と根拠

ORDレコード
ord-3b2e528c7b67401f983f1b1af7ec7833
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

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