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, 1 H), 7.20 (s, 1 H), 7.10 (d, 1 H), 2.78 (s, 3 H), 2.42 (s, 3 H); 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 record

ord-3262dfcd76f846518796ae0f5231d23d

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091228B2