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

HRID 1699963

반응식

HRID 1699963 반응식
[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]

참가 물질

6

반응물 4

HCID 887Methanol2회HCID 6344DichloromethaneHCID 94888N,N'-DiphenylformamidineHCID 155087421-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-96cbf6e7930c4379b9c167607494cd9b
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06348599B1

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