Sodium Sulfite → 3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepin-11-one
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[CH3:12][S:13][C:14]1[N:23]2[C:17](CC3C=CC=CC=3[CH:21]=[CH:22]2)=[N:16][N:15]=1.S([O-])([O-])=[O:29].[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:12][S:13]([C:14]1[N:23]2[C:17]([C:8](=[O:10])[C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=3[CH:21]=[CH:22]2)=[N:16][N:15]=1)=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under ice-cooling and stirring, 0.224 g of m-chloroperbenzoic acid was added to a solution of 0.243 g of 3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine in 4 ml of dichloromethane. The mixture was stirred for 30 minutes, after which 0.035 g of m-chloroperbenzoic acid was further added. After additional stirring for 1 hour, the reaction mixture was shaken well with an aqueous solution of sodium sulfite and a saturated aqueous solution of sodium hydrogen carbonate. The dichloromethane layer was washed with water and dried over Na2SO4. The solvent was evaporated off and the crystalline precipitate was recovered by filtration and washed with ethyl acetate. The above procedure gave 3-methylsulfinyl-11H-s-triazolo[3,4-b][3]benzazepin-11-one as crystals. Recrystallization from chloroform-methanol yielded colorless needles, m.p. 208°-211° C.
Workup
- temperatureUnder ice-cooling
- stirringThe mixture was stirred for 30 minutes
- stirringAfter additional stirring for 1 hour
- washThe dichloromethane layer was washed with water
- dry with materialdried over Na2SO4
- customThe solvent was evaporated off
- filtrationthe crystalline precipitate was recovered by filtration
- washwashed with ethyl acetate
Sources & evidence
- ORD record
- ord-861eaf04c4be4f87b7b525d31013af3e
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04150139
Reaction notes
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