Iodine → HCID 15239211, compound

Participants

Reaction Conditions

Reaction Steps

The general procedure of Krebs, Aust. J. Chem., 42, 1291 (1989), was employed. Ethyl 3-amino-4,4,4-trifluorocrotonate (9.16 g (gram), 50 mmol (millimole)) was dissolved in 30 mL (milliliter) of N,N-dimethylformamide and 1.2 g of 60 percent in mineral oil sodium hydride (50 mmol) was added in small portions with stirring and cooling to keep the temperature around 25° C. The mixture was stirred for about 1 hr (hour) until the evolution of gas had essentially ceased and was then cooled to -7° C. Carbon disulfide (4.19 g, 55 mmol) in 4 mL of N,N-dimethylformamide was then added slowly with stirring maintaining the temperature below 10° C. by cooling. The mixture was then allowed to warm to 15° C. and 8.29 g (60 mmol) of iodomethane in 4 mL of N,N-dimethylformamide was added with stirring. After 15 min (minutes) the reaction mixture was poured onto 75 g of ice. The red oil that formed was extracted into 2×75 mL of ether. The ethereal solution, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure and the residue was dissolved in 50 mL of ethanol and 7.91 g (100 mmol) of pyridine. A solution prepared by dissolving 12.7 g (50 mmol) of iodine and 20.75 g (125 mmol) of potassium iodide in 100 mL of water was added to this slowly with stirring. The precipitate that formed was collected by filtration and dissolved in ether. The ethereal solution was washed with water and 2×60 mL of 0.5N aqueous sodium thiosulfate solution, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was recrystallized from hexane to obtain 5.7 g (42 percent of theory) of the title compound as a solid melting at 64°-65° C.

Provenance & Evidence