Benzaldehyde → 3-methylthio-3-phenylmethyl-1,3-dihydro-2H-indol-2-one
Reaction equation
[C:1]1([CH2:7][CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)CC1=O.C(=O)C1C=CC=CC=1.CN(C)CCN(C)C.C([Li])CCC.[CH3:49][S:50]SC>O1CCCC1.O>[CH3:49][S:50][C:8]1([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -75 °C
Procedure
3-Phenylmethyl-1,3-dihydro-2H-indol-2-one (4 g, 18.25 mmol) (prepared from 1,3-dihydro-2H-indol-2-one and benzaldehyde by the method of Daisley and Walker J. Chem. Soc. (C) (1971) page 1373) and tetramethylethylenediamine (4.5 g, 38.7 mmol) was dissolved in freshly distilled tetrahydrofuran under nitrogen and cooled to -75° C. in an acetone/dry ice bath. n-Butyllithium (2.5M, 20 ml, 50 mmol) was added and the mixture was stirred at -75° C. for 30 minutes. Dimethyl disulfide (1.65 g, 17.6 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-methylthio-3-phenylmethyl-1,3-dihydro-2H-indol-2-one as a yellow oil which solidified on standing.
Workup
- temperatureto warm to room temperature
- concentrationthe mixture was concentrated under reduced pressure to a yellow oil
Sources & evidence
- ORD record
- ord-53eec181e35b424398cbe06f4d07688c
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05773448
Reaction notes
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