m-Chloroperbenzoic acid → 5-(m-Chlorobenzylsulfinyl)-2-pyridinecarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][N:6]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[O:28])=[CH:7][N:6]=1)=[O:4]Participants
4
Procedure
To the stirred solution of 10.28 g of 5-(m-chloro-benzylmercapto)-2-pyridinecarboxylic acid methyl ester in 150 ml of methylene chloride, cooled in an ice bath, 7.5 g of m-chloroperbenzoic acid are added in small portions during 10 minutes. The mixture is stirred for 3 hours, washed twice with 10% aqueous potassium bicarbonate, dried and evaporated. The residue is recrystallized from ethanol, to yield the 5-(m-chlorobenzylsulfinyl)-2-pyridinecarboxylic acid methyl ester of the formula ##STR6## melting at 143°-144°.