Potassium Iodide → HCID 60209559, compound

HRID 1640412Notes

Reaction equation

HRID 1640412 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[O:19])[CH2:14][CH2:13]2)=[N:10][CH:11]=1.[I-:26].[K+].C(=O)(O)[O-].[Na+]>O.S(=O)(=O)(O)O>[I:26][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]([NH:24][CH3:25])=[O:23])=[O:19])[CH2:14][CH2:13]2)=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 60209558HCID 60209558, compound

Product 1

HCID 60209559HCID 60209559, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 0.16 g (2.2 mmol) of sodium nitrite dissolved in 3.5 ml of water is slowly added to a solution, cooled to 0° C., of 0.47 g (1.5 mmol) of 2-(methylamino)-2-oxoethyl 4-(5-amino-2-pyridyl)-1-piperazinecarboxylate, prepared in step 5.4, in 15 ml of aqueous sulfuric acid solution (0.33N). Stirring is continued at about 0° C. for half an hour, and 0.83 g (5 mmol) of potassium iodide is slowly added. Stirring is continued at this temperature for half an hour and the reaction mixture is then maintained at 85° C. for 2 hours. After cooling to room temperature, the reaction medium is basified to pH=14, by adding saturated aqueous sodium bicarbonate solution. The aqueous phase is extracted three times with dichloromethane, the combined organic phases are washed with aqueous 35% thiosulfite solution, water, brine and dried over sodium sulfate. The filtrate is concentrated under reduced pressure and the residue thus obtained is purified by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol. After washing with diisopropyl ether, 0.35 g of product is obtained in the form of a beige-colored solid, and is used without further purification in the following step.

Workup

  1. additionis slowly added to a solution
  2. waitis continued at about 0° C. for half an hour
  3. stirringStirring
  4. waitis continued at this temperature for half an hour
  5. temperatureAfter cooling to room temperature
  6. extractionThe aqueous phase is extracted three times with dichloromethane
  7. washthe combined organic phases are washed with aqueous 35% thiosulfite solution, water, brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe filtrate is concentrated under reduced pressure
  10. customthe residue thus obtained
  11. customis purified by chromatography on silica gel
  12. washeluting with a 98/2 mixture of dichloromethane and methanol
  13. washAfter washing with diisopropyl ether

Sources & evidence

ORD record
ord-95196de82c3047f596c7a1f58deaebad
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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