tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide
Reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]([S@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5](/[CH:6]=[N:18]/[S@@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])=[CH:4][C:3]=1[CH3:11]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4-chloro-3,5-dimethyl-benzaldehyde (6.04 g, 35.8 mmol) and (R)-2-methylpropane-2-sulfinamide (4.78 g, 39.4 mmol) in toluene (110 mL) was treated with titanium(IV) isopropoxide (15.74 mL, 53.7 mmol). The mixture was stirred at 50° C. for 24 hours. It was then quenched with 10% aqueous sodium bicarbonate solution (100 mL) and filtered through Celite. The filter cake was washed with Et2O (250 mL). The organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).
Workup
- customIt was then quenched with 10% aqueous sodium bicarbonate solution (100 mL)
- filtrationfiltered through Celite
- washThe filter cake was washed with Et2O (250 mL)
- washThe organic layers were washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)
Sources & evidence
- ORD record
- ord-206b844d3daf4246a961576a997ed27b
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791100B2
Reaction notes
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