Methyl iodide → 3-methyl-3-methylthio-1,3-dihydro-2H-indol-2-one
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].CN(C)CCN(C)C.C([Li])CCC.I[CH3:25].[CH3:26][S:27]SC>O1CCCC1.O>[CH3:25][C:3]1([S:27][CH3:26])[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -75 °C
Procedure
1,3-Dihydro-2H-indol-2-one (3.3 g,25 mmol) and tetramethylethylenediamine (6.4 g, 55 mmol) was dissolved in freshly distilled tetrahydrofuran under nitrogen and cooled to -75° C. in an acetone/dry ice bath. n-Butyllithium (2.5M, 22 ml, 55 mmol) was added and the mixture was stirred at -75° C. for 30 minutes. Iodomethane (3.57 g, 25 mmol) was added and the mixture was allowed to warm to -20° C., the mixture was recooled to -75° C. then dimethyl disulfide (2.35 g, 25 mmol) was added and the mixture was allowed to warm to room temperature. Water (5 ml) was added and the mixture was concentrated under reduced pressure to a yellow oil. Column chromatography on silica gel (eluent ethyl acetate/hexane) gave 3-methyl-3-methylthio-1,3-dihydro-2H-indol-2-one as a yellow oil which solidified on standing.
Workup
- temperatureto warm to -20° C.
- customwas recooled to -75° C.
- temperatureto warm to room temperature
- concentrationthe mixture was concentrated under reduced pressure to a yellow oil
Sources & evidence
- ORD record
- ord-80ae6bce13e84227a296c9769a4bddde
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773448
Reaction notes
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