Acetic Acid → HCID 178474510, compound

Participants

Reaction Steps

N-{(2Z)-5-Methylene-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-2-ylidene}acetamide (4.51 g, 15.0 mmol, Intermediate A6) was dissolved into acetic acid (60 mL) and treated with 1 M iodine monochloride in dichloromethane (30 mL) over three minutes. After about 15 minutes more iodine monochloride solution (0.8 mL) was added, and after another ten minutes the solution was partially concentrated, and then concentrated twice from toluene. The residue was triturated with 20% ethyl acetate/toluene and the allyl chloride was collected by filtration. The filtrate was concentrated and redissolved into acetic acid (20 mL), treated with potassium acetate (2.95 g, 30 mmol), stirred 6 hours at room temperature, and concentrated thrice from ethyl acetate. The residue was mixed with a little ethyl acetate and filtered through basic alumina with a 2% methanol/ethyl acetate rinse. The filtrate was concentrated and chromatographed on silica (ethyl acetate/dichloromethane/hexanes) to give the title compound.

Provenance & Evidence