Methyl iodide → methyl 2-chloro-4-(N-methylmethylsulfonamido)benzoate

Reaction equation

IC.[C:3](=O)([O-])[O-].[Cs+].[Cs+].[Cl:9][C:10]1[CH:19]=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[Cl:9][C:10]1[CH:19]=[C:18]([N:20]([CH3:3])[S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

Procedure

78 μL of iodomethane and 447 mg of Cesium Carbonate were added to 300 mg of methyl 2-chloro-4-(methylsulfonamido)benzoate in 3 mL of DMF and stirred at room temperature for 16 hours. The reaction mixture was extracted in Ethyl Acetate twice with saturated bicarbonate and once with brine, dried over Magnesium Sulfate, filtered and concentrated to give crude methyl 2-chloro-4-(N-methylmethylsulfonamido)benzoate. 295 mg of methyl 2-chloro-4-(N-methylmethylsulfonamido)benzoate was hydrolyzed via Procedure M to yield 249 mg of 2-chloro-4-(N-methylmethylsulfonamido)benzoic acid.