Methyl iodide → 6-Methyl-2-(methylsulfanyl)-1,3-benzoxazole

6-Methyl-1,3-benzoxazole-2(3H)-thione (375 mg, 2.27 mmol) was dissolved in THF (2.0 mL), and iodomethane (1610.8 mg, 11.35 mmol) and potassium carbonate (627.36 mg, 4.54 mmol) were added. This reaction mixture was stirred vigorously at rt overnight. The reaction mixture was filtered and the solid was rinsed with additional THF. The filtrate was concentrated in vacuo to a yellow solid. The solid was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried with MgSO4, and concentrated. The solid was dried for 1 h in a 50° C. oven. The product 6-methyl-2-(methylsulfanyl)-1,3-benzoxazole was obtained as yellow-solid (145 mg, 35.6%). 1H NMR (300 MHz, DMSO-d6) δ 7.50 (d, 1H), 7.20 (s, 1H), 7.10 (d, 1H), 2.78 (s, 3H), 2.42 (s, 3H); LC-MS ret. time 2.90 min (method 2), m/z 180.1 (MH+).

1. filtrationThe reaction mixture was filtered
2. washthe solid was rinsed with additional THF
3. concentrationThe filtrate was concentrated in vacuo to a yellow solid
4. customThe solid was partitioned between ethyl acetate and water
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried with MgSO4
8. concentrationconcentrated
9. customThe solid was dried for 1 h in a 50° C. oven

ORD-Eintrag

ord-282e3e0b1304412690a1c8f242a8b9a7

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08013166B2