Potassium Iodide → HCID 21183185, compound

Participants

Reaction Steps

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.

Provenance & Evidence