Acetic Acid → HCID 21323360, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10]3=[N:12][N:13]=[C:14](SC)[N:9]3[CH:8]=[CH:7][C:6]=2[CH:17]=1.[S:18](=[O:22])(=O)(O)[OH:19].OO.S([O-])([O-])=O.[Na+].[Na+].[C:31](O)(=O)C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10]3=[N:12][N:13]=[C:14]([S:18]([CH3:31])(=[O:22])=[O:19])[N:9]3[CH:8]=[CH:7][C:6]=2[CH:17]=1Participants
Procedure
To a solution of 6.1 g of 8-methyl-3-methylthio-11H-s-triazolo[3,4-b][3]benzazepine in 75 ml of acetic acid was added 5.0 ml of concentrated sulfuric acid and under ice-cooling and stirring, 12.5 ml of 30% H2O2 was added dropwise. After stirring the mixture for 10 minutes at room temperature, it was heated on a water bath at 60°-65° C. for 2 hours. After ice-cooling, an aqueous solution of sodium sulfite was added to decompose the excess hydrogen peroxide. The solvent was evaporated off and, following addition of water, the residue was neutralized with concentrated aqueous ammonia, again under ice-cooling, and extracted with chloroform. The chloroform layer was washed with water and dried over Na2SO4. The solvent was evaporated off and the residue was treated with ether. By the above procedure was obtained 8-methyl-3-methylsulfonyl-11H-s-triazolo[3,4-b][3]benzazepine as crystals. Recrystallization from ethanol yielded colorless needles melting at 152°-153° C.
Workup
- temperatureunder ice-cooling
- stirringAfter stirring the mixture for 10 minutes at room temperature
- temperatureit was heated on a water bath at 60°-65° C. for 2 hours
- temperatureAfter ice-cooling
- customThe solvent was evaporated off
- additionaddition of water
- temperaturecooling
- extractionextracted with chloroform
- washThe chloroform layer was washed with water
- dry with materialdried over Na2SO4
- customThe solvent was evaporated off
- additionthe residue was treated with ether
Sources & evidence
- ORD record
- ord-0a922bacd59e439491327d8fca27fcba
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04150139
Reaction notes
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