Phthalic Anhydride → 2-(2-(1H-Benzo[d]imidazol-2-yl)ethyl)isoindoline-1,3-dione

HRID 1610794

Reaktionsgleichung

Reaktionsgleichung von HRID 1610794
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:15]1(=[O:20])[N:3]([CH2:4][CH2:5][C:6]2[NH:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=2)[C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Komponenten

6

Edukt 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 27880712-(2-Aminoethyl)benzimidazole dihydrochloride

Produkt 1

HCID 33521122-(2-(1H-Benzo[d]imidazol-2-yl)ethyl)isoindoline-1,3-dioneAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Aminoethylbenzimidazole dihydrochloride (Bull. Soc. Chim. Fr. 1991, 128, 255-259; 2.34 g, 10 mmol), phthalic anhydride (1.63 g, 11 mmol) and triethylamine (2.79 ml, 20 mmol) in chloroform (25 ml) were heated at reflux overnight, and the mixture was then cooled to room temperature, diluted with ethyl acetate and filtered off. The filtrate was washed with saturated sodium carbonate solution, buffer (pH=7) and saturated sodium chloride solution and dried over sodium sulphate. Chromatography (dichloromethane:methanol 10:1, Rf=0.4) gave 2.08 g of 2-(2-phthalimidylethyl)-benzimidazole (71.4% of theory) as a colourless foam. MS (DCI, NH3)=292 (M+H+). 1H-NMR (DMSO-d6): 3.15 (2H, t); 4.0 (2H, t); 7.05-7.2 (2H, m); 7.4-7.5 (2H, m); 7.8-7.9 (4H, m); 12.4 (1H, br s).

Aufarbeitung

  1. temperatureat reflux overnight
  2. filtrationfiltered off
  3. washThe filtrate was washed with saturated sodium carbonate solution, buffer (pH=7) and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-c13ace95260645c7905fe54833e5850b
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984642B1

Verknüpfte Notizen

Wird geladen…