Potassium Iodide → HCID 86618341, compound

HRID 1713054Notes

Reaction equation

HRID 1713054 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:18][CH3:19])[CH2:6][CH2:7][N:8]1[C:12]2=[N:13][S:14][C:15](N)=[C:11]2[S:10][C:9]1=[S:17])[CH3:2].N([O-])=O.[Na+].[I-:25].[K+].CCCCCC>Cl.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:18][CH3:19])[CH2:6][CH2:7][N:8]1[C:12]2=[N:13][S:14][C:15]([I:25])=[C:11]2[S:10][C:9]1=[S:17])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 8058HexaneHCID 23668193Sodium NitriteHCID 86618340HCID 86618340, compound

Product 1

HCID 86618341HCID 86618341, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 43 (280 mg, 0.925 mol) was suspended in 270 μl HCl (12 M) and water (400 μl). After stirring for 15 minutes the solution was cooled to 0° C. and sodium nitrite (127.6 mg, 1.85 mmol), dissolved in 1 ml water, was added dropwise. Stirring was continued for additional half an hour while maintaining the temperature below −5° C. Potassium iodide (307 mg, 1.85 mmol) dissolved in 1 ml water was added to the resulting mixture, which then turned dark brown. The reaction mixture was allowed to warm to 25° C. and stirring was continued overnight. Ethyl acetate was thereafter added, the phases were separated and the aqueous phase was further extracted with ethyl acetate. The combined organic phase was dried over Na2SO4, and the solvent was evaporated under reduced pressure to give 450 mg of the crude product. Purification by column chromatography using fine silica and a 4:1 hexane:ethyl acetate mixture as eluent gave 50 mg of Compound 44 (13% yield) as a white solid.

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. waitwas continued for additional half an hour
  4. temperaturewhile maintaining the temperature below −5° C
  5. additionwas added to the resulting mixture, which
  6. temperatureto warm to 25° C.
  7. stirringstirring
  8. waitwas continued overnight
  9. customthe phases were separated
  10. extractionthe aqueous phase was further extracted with ethyl acetate
  11. dry with materialThe combined organic phase was dried over Na2SO4
  12. customthe solvent was evaporated under reduced pressure
  13. customto give 450 mg of the crude product
  14. customPurification by column chromatography

Sources & evidence

ORD record
ord-f3e590380a1e4d20891952f1c350d361
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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