Potassium Iodide → HCID 23130809, compound

HRID 2080101Notes

Reaction equation

HRID 2080101 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Br[CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].[I-].[K+]>CN(C)C=O.O>[N:1]1[N:2]([CH2:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3[C:14](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]2=[O:22])[N:3]=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 178418936HCID 178418936, compound

Product 1

HCID 23130809HCID 23130809, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-1,2,3-triazole (2000 mg, 28.96 mmol) in N,N-dimethylformamide (60 mL) was added sodium hydride (1159 mg, 28.96 mmol, 60% in oil), which was stirred for 30 minutes. N-(3-Bromopropyl)phthalimide (7057 mg, 26.32 mmol) and potassium iodide (431 mg, 2.63 mmol) were added thereto, and the solution was stirred for 3 hours at 70°. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (dichloromethane-ethyl acetate), and the title compound (3526 mg, 13.75 mmol, 47%) was obtained.

Workup

  1. stirringthe solution was stirred for 3 hours at 70°
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-d46fbcfba73342c4ac460f1d19fc3f4b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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