1,10-Phenanthroline → 1,3-bis(1H-benzo[d]imidazol-1-yl)benzene

HRID 1044831ノート

反応式

HRID 1044831 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[NH:9]1[C:13]2[CH:14]=CC=C[C:12]=2[N:11]=[CH:10]1.[N:18]1[C:31]2[C:22](=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[CH:28][CH:27]=[CH:26]3)C=C[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl.[Cu]I.CO>[N:9]1([C:13]2[CH:14]=[CH:26][CH:27]=[C:28]([N:29]3[C:30]4[CH:25]=[CH:24][CH:23]=[CH:22][C:31]=4[N:18]=[CH:19]3)[CH:12]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:11]=[CH:10]1

参加物

9

反応物 4

HCID 13181,10-PhenanthrolineHCID 5798BenzimidazoleHCID 10796Cesium carbonateHCID 12270Benzene, 1,3-diiodo-

生成物 1

HCID 571821551,3-bis(1H-benzo[d]imidazol-1-yl)benzene収率 127.5%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 887Methanol溶媒2 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

In a 1 L round-bottomed flask 1,3-diiodobenzene (26.43 g, 80 mmol), 1H-benzo[d]imidazole (20.82 g, 176 mmol), and 1,10-phenanthroline (5.77 g, 32.0 mmol), CuI (3.05 g, 16 mmol), and cesium carbonate (120 g, 369 mmol) were combined in anhydrous DMF (350 mL) to give a brown suspension. The reaction was purged with N2 for 20 minutes and then heated to reflux for 24 hours. The reaction mixture was passed thought a plug of silica gel (5% MeOH in DCM) to obtain the crude product. The crude product was subjected to silica gel chromatography (SiO2, 400 g, 2% MeOH to 5% MeOH in DCM) to ultimately obtain the final product (12.66 g, 51%).

後処理

  1. customto give a brown suspension
  2. customThe reaction was purged with N2 for 20 minutes
  3. temperatureheated
  4. temperatureto reflux for 24 hours
  5. customto obtain the crude product

出典と根拠

ORDレコード
ord-0e0d1f61ce474fedacb57dd3be9fdb32
出典データセット
uspto-grants-2013_10
特許番号
US08563737B2

反応ノート

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