Sodium Iodide → HCID 18936771, compound

HRID 357004Notes

Reaction equation

HRID 357004 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]1=[O:11].[SH:12][C:13]1[N:18]2[CH:19]=[CH:20][N:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[N:21]1[CH:20]=[CH:19][N:18]2[C:13]([S:12][CH2:2][CH2:3][CH2:4][N:5]3[C:9](=[O:10])[CH2:8][S:7][C:6]3=[O:11])=[CH:14][CH:15]=[CH:16][C:17]=12

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18936755HCID 18936755, compoundHCID 178418687HCID 178418687, compound

Product 1

HCID 18936771HCID 18936771, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, 3.87 g (20 mmol) of 3-(3-bromopropyl)thiazolidine-2,4-dione was added to a suspension of 3.0 g (20 mmol) of 5-mercaptoimidazo[1,2-a]pyridine, 2.76 g (20 mmol) of potassium carbonate and 3.00 g (20 mmol) of sodium iodide in 100 ml of N,N-dimethylformamide was added, followed by stirring at room temperature for 64 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to yield 2.44 g (39.7%, light red-purple solid) of the desired product.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-e5e48bb80a934da9aa80c84f7a54a363
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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