Sodium Hydroxide → 1-methyl-5-(3-nitrophenyl)-1H-Tetrazole

Temperature

0 °C

In a dry flask N-methyl-3-nitro-benzamide (30.0 g, 167 mmol) was dissolved in acetonitrile (835 mL) and sodium azide (10.9 g, 167 mmol) was added and the reaction cooled in an ice bath. Triflic anhydride (29 mL, 172 mmol) was added dropwise to maintain the internal temperature below 3° C. The reaction mixture was stirred for 3.5 hours at 0° C. The reaction mixture was poured into IN aqueous sodium hydroxide (100 mL). The organic layer was separated dried with sodium sulfate, filtered, and concentrated in vacuo to 50 mL. The solution was diluted with dichloromethane and added water 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., 6.07 g (18%) of additional material was isolated upon filtration. further purification. 1H NMR (300 MHz, CDCl3), δ: 3.67 (m, 1H), 8.49 (dd, J=8, J′=2, 1H), 8.31 (d, J=8, 1H), 7.94 (dd, J=8, J′=8, 1H), 4.22 (s, 3H).

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

ORD record

ord-1ef218b8021c42e1867f8e07acd5c55b

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627629B2