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

HRID 407177

반응식

HRID 407177 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 887Methanol용매2회HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9575482e9f7241b28b3e5011e0c2f91e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754232B2

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