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

HRID 2227454ノート

反応式

HRID 2227454 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3653a529e44440ccb38978cef2f77d49
出典データセット
uspto-grants-2002_07
特許番号
US06413982B1

反応ノート

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