Phthaloyl chloride → 2-(1H-benzimidazol-2-yl)isoindole-1,3-dione

HRID 596573

Reaktionsgleichung

Reaktionsgleichung von HRID 596573
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11](Cl)(=[O:21])[C:12]1[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:14](Cl)=[O:15]>N1C=CC=CC=1>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[N:1]1[C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]2[C:11]1=[O:21]

Komponenten

4

Edukt 2

HCID 6955Phthaloyl chlorideHCID 136242-Aminobenzimidazole

Produkt 1

HCID 27557042-(1H-benzimidazol-2-yl)isoindole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Aminobenzimidazole (13.3 g.) is dissolved in 50 ml. of pyridine, and 10.2 g. of phthaloyl chloride is added, causing immediate precipitation. On mixing and heating on the steam-bath, all dissolves. The solution is heated 2 hours on the steam-bath with occasional swirling. It is cooled to room temperature and quenched in 200 ml. of water. After 1 hour agitation, the mixture is filtered free of solids and the solids washed with water. The yield of N-(benzimidazol-2-yl)phthalimide is 11.6 g. Recrystallization from glacial acetic acid results in bright yellow crystals of N-(benzimidazol-2-yl)phthalimide which, after drying, melts at 266°-268° C., λmax. 295.0, E11%cm. 529.

Aufarbeitung

  1. customprecipitation
  2. additionOn mixing
  3. temperatureheating on the steam-bath
  4. temperatureThe solution is heated 2 hours on the steam-bath
  5. customquenched in 200 ml
  6. filtrationthe mixture is filtered free of solids
  7. washthe solids washed with water
  8. customRecrystallization from glacial acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-d160830801d44ab1a98cbc6ebbc601fa
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011236

Verknüpfte Notizen

Wird geladen…