m-Chloroperbenzoic acid → HCID 23464484, compound
Reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6](=[O:29])[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolve 2 gm (0.0071 moles) of the ester of Example 2 in 200 cc of chloroform and 1.396 gm of m-chloroperbenzoic acid and stir at room temperature for 20 minutes. Add successive 100 mg portions of m-chloroperbenzoic acid until thin layer chromatography slows conversion of the starting material. Basify with calcium hydroxide and separate the solids. Chromotograph the solids over silica gel eluting with 30% ethyl acetate in benzene to obtain the title product (yield 870 mg).