Allyl iodide → 5-Chloro-3-(2-propen-1-yl)-1,3-benzothiazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

5-Chloro-1,3-benzothiazol-2(3H)-one (1.85 g, 10 mmol) was dissolved in DMF (50 ml) and treated with potassium carbonate (1.66 g, 12 mmol) and allyl iodide (1.1 ml, 12 mmol) then heated at 100° C. for 18 hrs. The solvent was then removed in-vacuo and the residue partitioned between water (100 ml) and ethyl acetate (2×100 ml). The organic layer was washed with saturated brine, separated and dried. Chromatography on silica gel eluting with a gradient of 10-50% ethyl acetate/40-60 petroleum ether gave the title compound as an oil that crystalised on standing (2.14 g, 95%).

Provenance & Evidence