N-Iodosuccinimide → HCID 90417079, compound

HRID 633565Notes

Reaction equation

HRID 633565 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:12]=[CH:11][N:10]([CH3:13])[C:5]2=[C:6]([O:8][CH3:9])[N:7]=1.[I:14]N1C(=O)CCC1=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:12]([I:14])=[CH:11][N:10]([CH3:13])[C:5]2=[C:6]([O:8][CH3:9])[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90417907HCID 90417907, compound

Product 1

HCID 90417079HCID 90417079, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 91B (0.82 g, 3.40 mmol) and N-iodosuccinimide (0.918 g, 4.08 mmol) were combined in dimethylformamide (17.01 mL), stirred for two hours at ambient temperature, and quenched with 100 mL of 10% aqueous sodium thiosulfate. The mixture was stirred for 15 minutes and the resulting solid was collected by filtration, washed repeatedly with water and dried to constant mass to afford the title compound (1.17 g, 94%).

Workup

  1. customquenched with 100 mL of 10% aqueous sodium thiosulfate
  2. stirringThe mixture was stirred for 15 minutes
  3. filtrationthe resulting solid was collected by filtration
  4. washwashed repeatedly with water
  5. customdried to constant mass

Sources & evidence

ORD record
ord-9ca283a0e7f54d5693c116ece92c2570
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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