Acetamide → 6-Nitro-1,2,3-benzothiadiazole

To a solution of 2-Amino-5-nitrobenzenethiol (5b) (6.0 g, 35.3 mmol) in n-BuOH (30 mL), cooled to 0° C., a solution of Isoamyl nitrite (5.0 mL, 37.1 mmol) in n-BuOH (30 mL) was added followed by conc. HCl (5.0 ml). The reaction mixture was warmed to room temperature and stirred for 5 h. To the resulting reaction mixture Acetamide (0.4 ml) was added and stirred for another 30 min at room temperature. After completion of reaction (by TLC), the reaction mixture was diluted with H2O (80 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine solution (100 mL), dried over Na2SO4 and concentrated under reduced pressure to obtain the crude material which was purified by column chromatography to afford 6-Nitrobenzo[d][1,2,3]thiadiazole (5c) (3.5 g, 54%) as a yellow solid.

1. additionwas added
2. stirringstirred for another 30 min at room temperature
3. customAfter completion of reaction (by TLC)
4. extractionextracted with EtOAc (3×150 mL)
5. washThe combined organic extracts were washed with brine solution (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto obtain the crude material which
9. customwas purified by column chromatography

ORD-Eintrag

ord-0bd5d5f23f43487db5d45f70b0f40c36

Quelldatensatz

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09133182B2