Dimethyl Sulfide → (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride
Reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][S:10][CH3:11].[CH3:12][C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.C(OCC)C>ClC(Cl)C>[Cl-:1].[CH3:12][C:13]1[NH:14][C:15]2[C:20]([C:21]=1[S+:10]([CH3:11])[CH3:9])=[CH:19][CH:18]=[CH:17][CH:16]=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
N-chlorosuccinimide (3.85 g, 29.35 mmole) was suspended in dichloroethane (40 ml) under a nitrogen atmosphere and cooled to −10° C. using an ice-salt-acetone bath. Dimethylsulfide (3 ml) was slowly added with stirring over a period of about 5 minutes. The mixture was stirred at this temperature for 10 minutes beyond the addition, at which time the ice-salt-acetone bath was replaced by a dry-ice acetone bath and the temperature was lowered to −50° C. To this solution was added 2-methylindole (3.85 g, 29.35 mmole) dissolved in dichloroethane (40 ml) slowly with stirring. The reaction mixture was stirred while allowing the temperature to reach 20° C. over about an hour. Diethyl ether (90 ml) was added with stirring and the precipitate which formed was filtered, washed well with ether, and dried overnight in a vacuum oven at room temperature. The free-flowing powder of (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride thus obtained was used without further purification in the following step.
Workup
- customwas replaced by a dry-ice acetone bath
- customwas lowered to −50° C
- stirringwith stirring
- stirringThe reaction mixture was stirred
- waitto reach 20° C. over about an hour
- stirringwith stirring
- customthe precipitate which formed
- filtrationwas filtered
- washwashed well with ether
- customdried overnight in a vacuum oven at room temperature
Sources & evidence
- ORD record
- ord-a65b2e5f84f64afcafd49ee0a267d32c
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06852726B2
Reaction notes
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