反应详情

温度

0 °C

N-Methyl-3-nitro-benzamide (30.0 g, 167 mmol) was dissolved in acetonitrile (835 mL), sodium azide (10.9 g, 167 mmol) was added and the mixture was cooled in an ice bath. Trifluoromethanesulfonic anhydride (29 mL, 172 mmol) was added dropwise at a rate which maintained the internal temperature below 3° C. The reaction mixture was stirred for 3.5 hours at 0° C. and then was poured into IN aqueous sodium hydroxide (100 mL). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum to 50 mL. The solution was diluted with dichloromethane and water was added to precipitate a yellow solid (18.46 g, 54%). A second crop of crystals was obtained by concentrated the filtrate in vacuo and adding it to boiling ethyl acetate. Upon cooling to 0° C., additional material (6.07 g, 18%) was isolated by filtration. 1H NMR (300 MHz, CDCl3), δ8.67 (m, 1H), 8.49 (dd, J=8, 2 Hz, 1H), 8.31 (d, J=8 Hz, 1H), 7.94 (dd, J=8, 8 Hz, 1H), 4.22 (s, 3H).

1. temperaturethe mixture was cooled in an ice bath
2. temperaturemaintained the internal temperature below 3° C
3. customThe organic layer was separated
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under vacuum to 50 mL
6. additionThe solution was diluted with dichloromethane and water
7. additionwas added
8. customto precipitate a yellow solid (18.46 g, 54%)
9. customA second crop of crystals was obtained
10. concentrationby concentrated the filtrate in vacuo
11. additionadding it
12. temperatureUpon cooling to 0° C.