Pyridine → 3-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide

3-Cyano-4-fluorobenzenesulfonyl chloride (10 g, 45.53 mmol) was added portion wise to a solution of 2-aminothiazole (5 g, 50.13 mmol) in dichloromethane (50 mL) and pyridine (18.4 mL, 228 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 1 hour a precipitate was observed. The mixture was stirred for 18 hours at room temperature. The mixture was sonicated for 2.5 hours until the solid had dissolved, then left to stir at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and azeotropically dried with toluene (2×100 mL). The residue was diluted carefully with a 1M aqueous solution of hydrogen chloride and stirred for 1 hour at room temperature whereupon a precipitate formed. The brown solid was collected by filtration and triturated with dichloromethane to afford the title compound as a brown solid (7.8 g, 60%).

1. customThe mixture was sonicated for 2.5 hours until the solid
2. dissolutionhad dissolved
3. waitleft
4. stirringto stir at room temperature for 18 hours
5. concentrationThe reaction mixture was then concentrated in vacuo
6. dry with materialazeotropically dried with toluene (2×100 mL)
7. additionThe residue was diluted carefully with a 1M aqueous solution of hydrogen chloride
8. stirringstirred for 1 hour at room temperature whereupon a precipitate
9. customformed
10. filtrationThe brown solid was collected by filtration
11. customtriturated with dichloromethane

ORD record

ord-d739c4fd94464a5a860ad38c3a1f5021

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772293B2