N-(pyridin-4-yl(tosyl)methyl)benzamide → N-(2-oxo-2-phenyl-1-(pyridin-4-yl)ethyl)benzamide
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7](S(C2C=CC(C)=CC=2)(=O)=O)[NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:2]=1>[I-].C[N+]1C(C)=C(CCO)SC=1>[O:16]=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:7]([NH:8][C:9](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
A flask containing a mixture of N-(pyridin-4-yl(tosyl)methyl)benzamide, 66 (10.0 g), and 3,4-dimethyl-5-(2-hydroxyethyl)-thiazolium iodide (1.1 g) is flushed with nitrogen for 15 min. Dichloromethane (150 mL) and benzaldehyde are added and the solution heated to 45° C., then triethylamine (42 mL) is added. After heating for 16 h, the solution is cooled to room temperature and saturated aqueous sodium hydrogen carbonate is added. The layers are separated, the aqueous phase extracted with additional dichloromethane, and the combined organic layers are washed with brine. Drying (magnesium sulfate), filtration, concentration and chromatography furnished the title compound, 67 (1.6 g).
Workup
- additionA flask containing
- customis flushed with nitrogen for 15 min
- additionDichloromethane (150 mL) and benzaldehyde are added
- additiontriethylamine (42 mL) is added
- temperatureAfter heating for 16 h
- temperaturethe solution is cooled to room temperature
- additionsaturated aqueous sodium hydrogen carbonate is added
- customThe layers are separated
- extractionthe aqueous phase extracted with additional dichloromethane
- washthe combined organic layers are washed with brine
- customDrying
- filtration(magnesium sulfate), filtration, concentration and chromatography
Sources & evidence
- ORD record
- ord-345fe3d7063a42db9e60eca5a3ae8213
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183285B2
Reaction notes
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