Sodium Iodide → 5-(Iodomethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole

Participants

Reaction Steps

A suspension of 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [4 g, 13.7 mmol; PCT Int. Appl. (2002), WO 0262774 A1] and sodium iodide (10.3 g, 68.6 mmol) in acetone (70 ml) was stirred at reflux temperature for 2 h under an argon atmosphere. The yellow precipitate was filtered off, the filtrate evaporated to dryness under reduced pressure and dissolved in tert-butyl methyl ether and brine/ice water 1/1. The aqueous layer was extracted one more time with tert-butyl methyl ether, the combined extracts washed with ice water/aqueous sodium thiosulfate, ice water/brine 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue recrystallized from tert-butyl methyl ether/heptane to give 2.5 g (6.5 mmol, 48%) of the title compound as yellow crystals.

Provenance & Evidence