1H-1,2,4-Triazole → 2-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dione

HRID 64850

Reaktionsgleichung

Reaktionsgleichung von HRID 64850
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]>CN(C)C=O>[N:1]1([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:17](=[O:18])[C:16]3[C:15](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]2=[O:23])[CH:5]=[N:4][CH:3]=[N:2]1

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 93575N-(4-Bromobutyl)phthalimide

Produkt 1

HCID 135888582-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dioneAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 9.0 g of 1H-1,2,4-triazole, 6.24 g of approximately 50% sodium hydride in oil and 130 ml of dimethylformamide was stirred for 1.5 hours, then 33 g of N-(4-bromobutyl)phthalimide was added and this mixture was heated on a steam bath for 6 hours, then concentrated to a solid residue. Water and methylene chloride were added, the organic layer was separated, washed with water, dried and concentrated to a residue. This residue was recrystallized from ethanol, giving 27.3 g of 2-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dione.

Aufarbeitung

  1. temperaturethis mixture was heated on a steam bath for 6 hours
  2. concentrationconcentrated to a solid residue
  3. additionWater and methylene chloride were added
  4. customthe organic layer was separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated to a residue
  8. customThis residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4a9c0cfa12ad4511837483c140d5bea2
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610981

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