Chlorosuccinimide → 2-(6-chloro-7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide
Reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:18]2[O:17][C:16](=[O:19])[N:15]([CH2:20][C:21]([NH2:23])=[O:22])[C:14]=2[CH:13]=[CH:12][CH:11]=1>S(=O)(=O)(O)O>[Cl:1][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:20][C:21]([NH2:23])=[O:22])[C:16](=[O:19])[O:17][C:18]=2[C:10]=1[F:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, N-chlorosuccinimide (0.635 g, 4.75 mmol) is added to a suspension of 2-(7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide 12 (1 g, 4.75 mmol) and sulfuric acid (90% w/w; 20 ml) at 0° C. The reaction is stirred 5 days then poured carefully into ice. The precipitate is collected by filtration and washed with water. The residue is recrystallized in EtOH/water (20/80 (v/v)) to afford 0.54 g of 2-(6-chloro-7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide 19.