Methanol → 1-(5-Carboxypentyl)-2-(N-phenyl-2-aminovinyl)-3,3-dimethylindolium bromide

HRID 1699963

反応式

HRID 1699963 の反応式
[Br-:1].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:20])([CH3:19])[C:11]=1[CH3:21])([OH:4])=[O:3].[C:22]1([NH:28][CH:29]=NC2C=CC=CC=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO.ClCCl>C(O)(=O)C>[Br-:1].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N+:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:20])([CH3:19])[C:11]=1[CH:21]=[CH:29][NH:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:4])=[O:3]

参加物

6

反応物 4

HCID 887Methanol2 回HCID 6344DichloromethaneHCID 94888N,N'-DiphenylformamidineHCID 155087421-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide

生成物 1

HCID 700023921-(5-Carboxypentyl)-2-(N-phenyl-2-aminovinyl)-3,3-dimethylindolium bromide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

1-(5-carboxypentyl)-2,3,3-trimethylindolium bromide (1.77 g, 5 mmol) and N,N′-diphenylformamidine (1.96 g, 10 mmol) were mixed in acetic acid (15 m); the resulting mixture was then heated at reflux. The reaction was monitored by UV/VIS spectroscopy (methanol solution, product absorbance λmax 398 nm) and TLC (silica. Methanol, 20: dichloromethane, 80; product runs as a yellow streak, Rf 0.1-0.25). After 2.5 hrs the orange-red solution was then left to cool over 16 hrs, then the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica. 5-20% methanol/dichloromethane) to give the title compound [1.3] as a yellow-orange foam after drying, 1.5 g (66%).

後処理

  1. temperaturethe resulting mixture was then heated
  2. temperatureat reflux
  3. temperatureto cool over 16 hrs
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by flash chromatography (silica. 5-20% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-96cbf6e7930c4379b9c167607494cd9b
出典データセット
uspto-grants-2002_02
特許番号
US06348599B1

関連ノート

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