Acetic Acid → 8-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one-6-oxide
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.C(O)(=[O:20])C>>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[C:7]3[C:12]([CH2:13][S:14](=[O:20])[C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3Participants
3
Procedure
A solution of 8-chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one (250 mg) in acetic acid (5 ml) was stirred for 5 minutes. NaBO3 (105 mg) was added and the mixture was stirred for 7 hours. The reaction was quenched with 5% NaOH and extracted with CH2Cl2, and the extracts were washed with brine, dried (MgSO4), filtered and concentrated to afford a tan solid (270 mg). This was chromatographed on silica to afford the crude sulfoxide (250 mg) as a tan solid containing some starting material; MS (CI, M+H)=278.
Workup
- customThe reaction was quenched with 5% NaOH
- extractionextracted with CH2Cl2