Cesium carbonate → 2-[2-(1H-1,2,3-Triazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione

HRID 558150Notes

Reaction equation

HRID 558150 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.Br[CH2:7][CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:1]1([CH2:7][CH2:8][N:9]2[C:10](=[O:19])[C:11]3[C:12](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:14])[CH:5]=[CH:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 178418936HCID 178418936, compound

Product 1

HCID 534206642-[2-(1H-1,2,3-Triazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

Add 1H-1,2,3-triazole (250 g; 3.51 mol), N-(2-bromoethyl)phthalimide (942 g; 3.52 mol) and 1500 mL of DMF to a 5-L roundbottom flask fitted with a mechanical stirrer, nitrogen inlet and temperature probe. Cool the mixture to 15° C. Stir the mixture until all of the solids are nearly dissolved and then cool in an ice-water bath. Add cesium carbonate (1145 g; 3.51 mol) in portions over 10 min. The reaction mixture exotherms to 21° C. Allow the mixture to stir and come to RT overnight. Pour the reaction mixture into a 12-L flask containing 8 L of ice-water. Stir the suspension for 30 min and then filter and rinse the solid with 3 L of water. Air-dry for 2 h. Recrystallize the mixture of regioisomers from 7 L of absolute ethanol. Isolate the solid by filtration and air-dry. Recrystallize again from 16 L of absolute ethanol. Isolate the solids by filtration and rinse with fresh ethanol (1000 mL). Vacuum-dry the solids at 40° C. to give the title compound, 292.7 g (34%) as a white solid. MS (EI) m/z 243 [M+1]+.

Workup

  1. customfitted with a mechanical stirrer, nitrogen inlet
  2. dissolutionare nearly dissolved
  3. temperaturecool in an ice-water bath
  4. customexotherms to 21° C
  5. stirringAllow the mixture to stir
  6. additionPour the reaction mixture into a 12-L flask
  7. stirringStir the suspension for 30 min
  8. filtrationfilter
  9. washrinse the solid with 3 L of water
  10. customAir-dry for 2 h
  11. customRecrystallize
  12. additionthe mixture of regioisomers from 7 L of absolute ethanol
  13. customIsolate the solid
  14. filtrationby filtration
  15. customair-dry
  16. customRecrystallize again from 16 L of absolute ethanol
  17. customIsolate the solids
  18. filtrationby filtration
  19. washrinse with fresh ethanol (1000 mL)
  20. customVacuum-dry the solids at 40° C.

Sources & evidence

ORD record
ord-0682f35f924e49488bf77493429cbba7
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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