m-Chloroperbenzoic acid → 20290-48-6

Reaction equation

C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH:12]1[C:17]2[C:18](=[O:27])[NH:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[S:22][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:12]1[C:17]2[C:18](=[O:27])[NH:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[S:22](=[O:9])[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

Procedure

A solution of MCPBA (1 eq) in chloroform (5 ml) was added to a stirred solution of 10,11-dihydrodibenzo[b,f][1,4] thiazepin-11-one (114 mg, 0.5 mmol) in chloroform (30 ml). After 0.5 hr the reaction mixture was poured into sodium bicarbonate solution (5%, 30 ml), separated and the aqueous layer washed with chloroform (30 ml). The combined organic fractions were dried (MgSO4) and evaporated. Recrystallisation from toluene gave the title compound as off-white crystals (76 mg, m.p. 308°-310° C., Rf 0.16, CH2Cl2 /MeOH 50:1).