Sodium Iodide → 2-(Iodomethyl)-5-(trifluoromethyl)benzothiazole

Temperature

55 °C

To a stirred solution of 10.79 g (42.97 mmol) of 2-(chloromethyl)-5-(trifluoromethyl)benzo[d]thiazole (Compound 3) in 86 mL of acetone was added 7.40 g (49.42 mmol) of sodium iodide. The resulting reaction mixture was heated to 55° C. for 1 hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between EtOAc and water, the layers separated, and the organic layer washed with water (1×). The recovered organic layer was then treated with 1.0 M Na2S2O3 and stirred vigorously for 15 minutes. The layers were then separated and the organic layer washed sequentially with water (1×) and brine (1×). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 14.28 g (97% crude yield) of 2-(iodomethyl)-5-(trifluoromethyl)benzo[d]thiazole (Compound 5) that was used without further purification: 1H NMR (CDCl3, 300 MHz): δppm 8.26 (s, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.66 (d, J=8.4 Hz, 1H), 4.80 (s, 2H).

1. customThe resulting reaction mixture
2. temperatureThe reaction mixture was cooled to ambient temperature
3. concentrationconcentrated in vacuo
4. customThe residue was partitioned between EtOAc and water
5. customthe layers separated
6. washthe organic layer washed with water (1×)
7. additionThe recovered organic layer was then treated with 1.0 M Na2S2O3
8. customThe layers were then separated
9. washthe organic layer washed sequentially with water (1×) and brine (1×)
10. dry with materialThe organic layer was dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-3c84eac5a02f4be09df1f0df0d70e388

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916563B2