Sodium Iodide → HCID 18936666, compound

HRID 357100Notes

Reaction equation

HRID 357100 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:23](=[O:24])[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:21]2[S:31](=[O:35])(=[O:34])[CH2:32][CH2:33][N:20]2[C:19]1=[O:36].[I-].[Na+]>CN(C)C=O.O>[N:12]1[CH:11]=[CH:10][N:9]2[C:4]([S:3][CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:23](=[O:24])[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:21]4[S:31](=[O:35])(=[O:34])[CH2:32][CH2:33][N:20]4[C:19]3=[O:36])=[CH:5][CH:6]=[CH:7][C:8]=12

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 18936674HCID 18936674, compoundHCID 178418687HCID 178418687, compound

Product 1

HCID 18936666HCID 18936666, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60 mg (1.5 mmol) of 60% oily sodium hydride in 10 ml of N,N-dimethylformamide, 225 mg (1.5 mmol) of 5-mercaptoimidazo[1,2-a]pyridine was added at room temperature, followed by stirring for 10 minutes. To this mixture, 480 mg (1.3 mmol) of 6-(4-chlorobutyl)-1,1-dioxo-8-phenyl-2,3-dihydro-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione and 225 mg (1.5 mmol) of sodium iodide were added, followed by stirring at 80° C. for 3 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate 3 times. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1) to yield 400 mg (65.7%, white foamy substance) of the desired product.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at 80° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate 3 times
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-10e1c72051e643ac9433df2575377790
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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