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

HRID 1719692Notes

Reaction equation

HRID 1719692 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].BrCCCC[C:13]1[CH:23]=[CH:22][CH:21]=[C:15]2[C:16]([NH:18][C:19](=[O:20])[C:14]=12)=[O:17]>CN(C)C=O>[N:1]1([CH2:23][CH2:13][CH2:14][CH2:15][N:18]2[C:19](=[O:20])[C:14]3[C:15](=[CH:21][CH:22]=[CH:23][CH:13]=3)[C:16]2=[O:17])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 21960043Bromobutylphthalimide

Product 1

HCID 135888582-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dioneYield 172.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of about 9.0 g of 1H-1,2,4-triazole, about 6.24 g of approximately 50% sodium hydride in oil and about 130 ml of dimethylformamide was stirred for about 1.5 hours, then about 33 g of bromobutylphthalimide was added and this mixture was heated on a steam bath for about 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 about 27.3 g of 2-[4-(1H-1,2,4-triazol-1-yl)butyl]-1H-isoindol-1,3(2H)-dione.

Workup

  1. temperaturethis mixture was heated on a steam bath for about 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

Sources & evidence

ORD record
ord-e06ed718030148768f51e6ff4fd4c647
Source dataset
uspto-grants-1985_09
Patent number
US04542145

Reaction notes

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