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

HRID 2083982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2083982
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. Chem. 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 (DCl, NH3)=292 (M+H+). 1H-NMR (DMSO-d6): 3.15 (2H, t); 4.0 (2H, t); 7.05-71 (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-cd5ccf2e350e470090449f8dd9f1b08a
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716849B1

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