Sodium Iodide → HCID 59420810, compound

HRID 499065Notes

Reaction equation

HRID 499065 reaction equation
[I-:1].[Na+].Cl[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=2)[N:5]=1.[IH:23]>>[I:1][C:4]1[CH:9]=[C:8]([I:23])[N:7]=[C:6]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[CH:14][CH:13]=2)[N:5]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 86616256HCID 86616256, compound

Product 1

HCID 59420810HCID 59420810, compoundYield 78%

Conditions

Temperature
70 °C

Procedure

Sodium iodide (13.5 g, 90 mmol) was added to a solution of N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)propionamide (5 g, 15 mmol) in 60% HI (50 ml). The reaction mixture was stirred at 70° C. for 10 h. The suspension was filtered. The recovered solid was taken up in saturated sodium bicarbonate aqueous solution (˜200 ml). Extractions were carried out with ethyl acetate (3×100 ml). The organic was washed with saturated sodium bicarbonate solution and brine. The solid was triturated in a minimum of dichloromethane to afford the title compound as a white solid (6 g, 78%). ES+ 512.

Workup

  1. filtrationThe suspension was filtered
  2. extractionExtractions
  3. washThe organic was washed with saturated sodium bicarbonate solution and brine
  4. customThe solid was triturated in a minimum of dichloromethane

Sources & evidence

ORD record
ord-dd3fc5fdbc734939b9646c322f25943f
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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