Methyl iodide → 5-Chloro-2-(methylsulfinyl)benzo[d]oxazole

Iodomethane (1.35 mL, 21.6 mmol) was added to a mixture of 5-chlorobenzo[d]oxazole-2(3H)-thione (2.00 g, 10.8 mmol) and K2CO3 (2.99 g, 21.6 mmol) in THF (43 mL). After 2 h, the reaction mixture was filtered and concentrated under reduced pressure. The crude material was dissolved in CH2Cl2 (40 mL) and meta-chloroperbenzoic acid (50-55%, 3.73 g, 10.8 mmol) was added at 0° C. The reaction was allowed to warm to rt. After stirring overnight, the reaction mixture was diluted with sodium thiosulfate (saturated, aqueous) and the organics were separated. The organics were washed with NaHCO3 (saturated, aqueous, 50 mL) and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 3.32 g (>100% crude yield) of the desired product as an orange solid. The material was used without further purification. LC-MS: RT=6.60 min., [M+H]+=216.2.

1. filtrationthe reaction mixture was filtered
2. concentrationconcentrated under reduced pressure
3. dissolutionThe crude material was dissolved in CH2Cl2 (40 mL)
4. customthe organics were separated
5. washThe organics were washed with NaHCO3 (saturated, aqueous, 50 mL) and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe material was used without further purification

ORD record

ord-67a4d463a2254d9da7ab82d6208349dd

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822472B2