Potassium Iodide → HCID 21183185, compound

HRID 1386884Notes

Reaction equation

HRID 1386884 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH3:10])[C:3]=1N.N([O-])=O.[Na+].[I-:15].[K+].S(=O)(O)[O-].[Na+]>Cl.O.ClCCl>[Cl:1][C:2]1[C:3]([I:15])=[C:5]([S:9][CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 6407022-Chloro-6-(methylthio)benzenamineHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 21183185HCID 21183185, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-6-methylthioaniline (15.0 g, 87 mmol) was dissolved in 200 mL of concentrated hydrochloric acid and the resulting solution was cooled to 0° C. to −10° C. with a dry ice/methanol bath. A solution of 8.9 g (130 mmol) of sodium nitrite in 30 mL of water was added dropwise with stirring and cooling to maintain the temperature below 0° C. The solution was then stirred for 20 min at 0° C. A mixture of 22 g (130 mmol) of potassium iodide dissolved in 300 mL of water and 200 mL of dichloromethane was prepared and the solution prepared above was added to it in portions with stirring. The mixture was allowed to react for 20 min at ambient temperature. A small amount of aqueous sodium bisulfite solution was added and then the phases were separated. The organic phase was washed twice with 2N aqueous hydrochloric acid and once with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was crystallized with heptane and chromatographed on silica eluting with an 85:15 mixture of hexane and dichloromethane to obtain 13.5 g of the title compound as a crystalline, low melting yellow solid.

Workup

  1. temperaturethe resulting solution was cooled to 0° C. to −10° C. with a dry ice/methanol bath
  2. temperaturecooling
  3. temperatureto maintain the temperature below 0° C
  4. stirringThe solution was then stirred for 20 min at 0° C
  5. customthe solution prepared
  6. additionabove was added to it in portions
  7. stirringwith stirring
  8. customto react for 20 min at ambient temperature
  9. customthe phases were separated
  10. washThe organic phase was washed twice with 2N aqueous hydrochloric acid and once with saturated aqueous sodium chloride solution
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated by evaporation under reduced pressure
  13. customThe residue was crystallized with heptane
  14. customchromatographed on silica eluting with an 85:15 mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-1e5da86e57ba4f42b1fbc42d1fbc8989
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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