Ethanol → HCID 20338082, compound
Reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:3]1=2.S(=O)(=O)(O)O.[CH2:27]([OH:29])[CH3:28]>>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([O:29][CH2:27][CH3:28])=[O:19])=[CH:16][C:3]1=2Participants
4
Procedure
To 200 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]thiepin-2-yl)-propionamide in 4 ml of ethanol was added 0.4 ml of conc. sulfuric acid and the mixture was refluxed with stirring for 1 hour. The solvent was distilled off to obtain the residue, to which was added pieces of ice, and the mixture was extracted with ethyl acetate and the extract was washed with saturated sodium hydrogen carbonate, then saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain brown oil, which was chromatographed over silica gel, and eluted with benzene-chloroform. There was obtained 141 mg of ethyl 2-(10,11-dihydro-11-oxo dibenzo[b,f]-thiepin-2-yl)-propionate as pale yellow oil.
Workup
- temperaturethe mixture was refluxed
- distillationThe solvent was distilled off
- customto obtain the residue
- additionto which was added pieces of ice
- extractionthe mixture was extracted with ethyl acetate
- washthe extract was washed with saturated sodium hydrogen carbonate
- dry with materialsaturated sodium chloride solution and dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
- customto obtain brown oil, which
- customwas chromatographed over silica gel
- washeluted with benzene-chloroform
Sources & evidence
- ORD record
- ord-9e9aa83adadb46e09f2c23d3caa321b8
- Source dataset
- uspto-grants-1980_05
- Patent number
- US04205170
Reaction notes
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