Methyl iodide → N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide

Ex-101A: A solution of N-(4-acetyl-phenyl)-methanesulfonamide (Ex-100A, 2.0 g, 9.4 mmol) in anhydrous DMF (300 mL) was treated with potassium carbonate (2.59 g, 18.8 mmol), followed by the addition of methyl iodide (5.85 mL, 94 mmol). The reaction mixture refluxed for two hours and was then treated with more methyl iodide (5.85 mL, 94 mmol). The reaction refluxed for another two hours, and reaction completeness was confirmed by HPLC analysis. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was collected, dried over sodium sulfate, and concentrated to a clear oil with residual DMF. Water (25 mL) was added to precipitate a white solid. The white solid was then filtered and dried by vacuum oven at 20° C. (−20 mm Hg) to give 1.37 g (64%) of N-(4-acetyl-phenyl)-N-methyl-methanesulfonamide. 1H-NMR (CDCl3) δ 7.88 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.86 (s, 3H), 2.60 (s, 3H). HRMS m/z: calc. 530.1307, found 530.1313.

1. temperatureThe reaction mixture refluxed for two hours
2. temperatureThe reaction refluxed for another two hours
3. customreaction completeness
4. customThe reaction was quenched with water (100 mL)
5. extractionextracted with ethyl acetate (2×100 mL)
6. customThe organic phase was collected
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated to a clear oil with residual DMF
9. additionWater (25 mL) was added
10. customto precipitate a white solid
11. filtrationThe white solid was then filtered
12. customdried by vacuum oven at 20° C. (−20 mm Hg)

ORDレコード

ord-5821600eb019413e80b830f69e75ec23

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07094801B2