Water → 2-[(1,2,4-Oxadiazol-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 966945Notes

Reaction equation

HRID 966945 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.Cl[CH2:13][C:14]1[N:18]=[CH:17][O:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:16]1[CH:17]=[N:18][C:14]([CH2:13][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[N:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 10796Cesium carbonateHCID 27357653-(Chloromethyl)-1,2,4-oxadiazole

Product 1

HCID 222927542-[(1,2,4-Oxadiazol-3-yl)methyl]-1H-isoindole-1,3(2H)-dioneYield 83.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Phthalimide (892 mg, 6.01 mmol) was dissolved in DMF (10 mL) followed by addition of 3-(chloromethyl)-1,2,4-oxadiazole (713 mg, 6.01 mmol), cesium carbonate (2.95 g, 9.02 mmol) and tetrabutylammonium iodide (3.35 g, 8.02 mmol), and then the mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, and the resulting precipitate was collected by filtration and dried under reduced pressure to give N-(1,2,4-oxadiazol-3-ylmethyl)phthalimide (1.15 g; yield 83%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-527e9d2a07ea4bd6ae36a2330f1c799b
Source dataset
uspto-grants-2005_10
Patent number
US06953785B2

Reaction notes

Loading…