Triethylamine → 5-Fluorobenzo-2,1,3-thiadiazole

4-Fluoro-benzene-1,2-diamine (2.5 g, 19.8 mmol) was added into a 50-mL Schlenk flask. The system was flushed with argon before 200 mL of chloroform was added and followed by addition of triethylamine (11.05 mL, 79.3 mmol). A clear solution was observed after stirring at room temperature for 10 minutes. Thionyl chloride (5.18 g, 43.6 mmol) was added dropwise. The mixture was heated to reflux for 5 hours before being cooled down to room temperature. The organic layer was washed with brine (100 mL) and further dried over anhydrous MgSO4. After removal of the solvent, the product was purified by silica gel column with hexane/dichloromethane (v/v, 1/2) as the eluent. Removal of the solvent offered a colorless oil (1.35 g, 44.3% yield) after being dried in vacuo. 1H NMR (CDCl3, 500 MHz): δ 7.93 (d×d, 1H, J=9.0 Hz×5.0 Hz), δ 7.56 (d×d, 1H, J=9 Hz×2.5 Hz), δ 7.38 (m, 1H).

1. customThe system was flushed with argon before 200 mL of chloroform
2. additionwas added
3. temperatureThe mixture was heated
4. temperatureto reflux for 5 hours
5. temperaturebefore being cooled down to room temperature
6. washThe organic layer was washed with brine (100 mL)
7. dry with materialfurther dried over anhydrous MgSO4
8. customAfter removal of the solvent
9. customthe product was purified by silica gel column with hexane/dichloromethane (v/v, 1/2) as the eluent
10. customRemoval of the solvent

ORD record

ord-137972efc3ec40f4a226bca8d074ea34

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08723028B2