Methyl iodide → 2-(Methylthio)benzoxazole

Method A, Part A. A solution of 2-mercapto-1H-benzoxazole (5.85 g, 38.7 mmol), methyl iodide (2.70 mL, 43.4 mmol), and potassium carbonate (7.39 g, 53.5 mmol) in tetrahydrofuran (100 mL) was heated to reflux for 18 hours. After stirring at room temperature for an additional 24 hours, the solution was poured into (2×150 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford sufficiently pure 2-methylthio-1-H-benzoxazole (6.27 g, 37.9 mmol, 98%) as a pale yellow oil. This material was dissolved in methylene chloride (100 mL), cooled to 0° C., and treated with a solution of m-chloroperben-zoic acid (7.20 g, 41.7 mmol) in methylene chloride (40 mL). Sodium bicarbonate (about 10 g) was added, and the mixture was stirred for 18 hours. This mixture was diluted slightly with methylene chloride, then washed with aqueous sodium carbonate solution (1M, 2×150 mL) and water (150 mL). The aqueous phases were back-extracted in sequence with methylene chloride (150 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to afford the product, 2-methylsulfonyl-1H-benzoxazole (7.04 g, 35.7 mmol, 94%), as a waxy solid. 1H NMR (CDCl3): 8.03-7.40 (4H, m); 3.22 (3H, s).

1. temperatureto reflux for 18 hours
2. additionthe solution was poured into (2×150 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customevaporated

ORD record

ord-5cc9c244922b458a9edbdb7e8873193c

Source dataset

uspto-grants-1994_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05364875