Methyl iodide → HCID 178503083, compound

To a solution of acetophenone (5.0 g, 41.6 mmol) and CS2 (3.17 g, 41.6 mmol) in THF (150 mL) was added sodium hydride (1.997 g, 83 mmol) at 0° C. After 30 min at 0° C., the reaction was warmed to room temperature and stirred for 1 h, then refluxed for 4 h. The reaction was cooled to room temperature, added iodomethane (16.23 g, 104 mmol), and refluxed for another 12 h. The reaction was cooled and extracted with ethyl acetate. The organic extracts were concentrated under reduced pressure. The residue was diluted with ethanol (200 mL), added hydrazine (1.334 g, 41.6 mmol), and refluxed for 4 h. After cooling, the mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (6.02 g). LCMS m/z=191.37 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.31 (s, 3H), 6.21 (s, 1H), 7.38-7.56 (m, 5H), 12.2 (s, 1H).

1. temperaturerefluxed for 4 h
2. temperatureThe reaction was cooled to room temperature
3. temperaturerefluxed for another 12 h
4. temperatureThe reaction was cooled
5. extractionextracted with ethyl acetate
6. concentrationThe organic extracts were concentrated under reduced pressure
7. additionThe residue was diluted with ethanol (200 mL)
8. temperaturerefluxed for 4 h
9. temperatureAfter cooling
10. concentrationthe mixture was concentrated under reduced pressure
11. extractionextracted with ethyl acetate
12. dry with materialThe organic extracts were dried over MgSO4
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified by silica gel column chromatography

ORD record

ord-fd5815c9d858487d939490a379418faf

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012478B2