Pyridine → HCID 54300325, compound

Reaction equation

C[NH:2][C:3]1[C:4](=[CH:8][C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])[C:5]([OH:7])=[O:6].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.N1C=CC=C[CH:26]=1>C(Cl)(Cl)Cl>[CH3:26][O:7][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:3]=1[NH:2][S:21]([C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

Procedure

To a solution of 2.00 g (0.011 mmol) of methyl 3,5-dimethylanthranilic acid in 10.0 mL of pyridine was added 2.17 (0.011 mmol) of 4-fluorobenzenesulfonyl chloride. The reaction mixture was stirred for 24 h at room temperature and then diluted with chloroform and washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes and the resulting solid was filtered and dried to provide 3.09 g (82%) of the desired product as a white solid. Electrospray Mass Spec: m/z 338.3 (M+H)+.