Methane → 4-Ethyl-4-phenyl-2-(2-phenylquinolin-4-yl)-imidazoline

HRID 2227454노트

반응식

HRID 2227454 반응식
[C:1]1([C:7]([NH2:12])([CH2:10][CH3:11])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.C.CO[C:20]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[C:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:23]=1)=O>C1(C)C=CC=CC=1.CO.C(Cl)Cl.O>[CH2:10]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][NH:9][C:20]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:23]=2)=[N:12]1)[CH3:11]

참가 물질

9

반응물 4

HCID 297MethaneHCID 211492-Phenylbutane-1,2-diamineHCID 609693Methyl 2-phenyl-4-quinolinecarboxylateHCID 16682925Trimethylaluminum

생성물 1

HCID 1784352444-Ethyl-4-phenyl-2-(2-phenylquinolin-4-yl)-imidazoline

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매3회HCID 6344Dichloromethane용매

실험 절차

2-Phenylbutane-1,2-diamine (328 mg, 2.0 mmol) in 4.4 mL of toluene is added dropwise to a stirred solution of trimethylaluminum (2.0 M, 1 mL) in 5 mL of toluene at below 10° C. under nitrogen. At the end of methane evolution, methyl-2-phenyl-4-quinolinecarboxylate (263 mg, 1 mmol) in 2 mL of toluene is gradually added at room temperature. The reaction mixture is refluxed for 3 hours under nitrogen. After cooling, the solution is treated with 1 mL of water, diluted with 1 mL of methanol and 1 mL of methylene chloride, and refluxed for 15 minutes. After separation of organic solvent and solvent evaporation, the residue is purified over silica gel chromatography eluting with 5-10% MeOH/CH2Cl2. The corresponding compound is obtained as a white solid.

후처리

  1. temperatureThe reaction mixture is refluxed for 3 hours under nitrogen
  2. temperatureAfter cooling
  3. temperaturerefluxed for 15 minutes
  4. customAfter separation of organic solvent and solvent evaporation
  5. customthe residue is purified over silica gel chromatography
  6. washeluting with 5-10% MeOH/CH2Cl2
  7. customThe corresponding compound is obtained as a white solid

출처 및 근거

ORD 기록
ord-3653a529e44440ccb38978cef2f77d49
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06413982B1

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