Dimethylformamide → HCID 90417079, compound

HRID 633606Notes

Reaction equation

HRID 633606 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:11]=[CH:10][N:9]([CH3:12])[C:5]2=[C:6](Cl)[N:7]=1.CN(C)[CH:15]=[O:16].[I:18]N1C(=O)CCC1=O.S(=O)(=O)(O)[O-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]([I:18])=[CH:10][N:9]([CH3:12])[C:5]2=[C:6]([O:16][CH3:15])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 516919Sodium BisulfateHCID 90416413HCID 90416413, compound

Product 1

HCID 90417079HCID 90417079, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Example 187A (3.24 g, 13.44 mmol) and dimethylformamide (37 mL) was cooled to 0° C. After the addition of 1-iodopyrrolidine-2,5-dione (3.6 g, 16.00 mmol), the reaction mixture was stirred at ambient temperature for 3 hours. The solution was cooled to 0° C. and 60 mL water was added followed by aqueous sodium bisulfate (60 mL, 10%) solution. The mixture was stirred for 1 hour at ambient temperature. Solid was collected by filtration, rinsed with water and was dried under vacuum to provide 4.9 g (99%) of the title compound.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe mixture was stirred for 1 hour at ambient temperature
  3. filtrationSolid was collected by filtration
  4. washrinsed with water
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-1151f020ccb546578ad255a72c095164
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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