Methyl iodide → alpha-(p-Tolylthio)-alpha-(m-phenoxyphenyl)propionitrile
Reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[C:9]#[N:10])=[CH:3][CH:2]=1.[CH3:25][O-].[Na+].CI.[Cl-].[NH4+]>CO>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)([CH3:25])[C:9]#[N:10])=[CH:5][CH:6]=1Participants
Procedure
1.245 g of alpha-(p-tolylthio)(m-phenoxyphenyl)-acetonitrile was dissolved in 5 ml of anhydrous methanol, and a 2.2 M methanol solution of sodium methoxide was added at room temperature in an atmosphere of argon. The mixture was stirred, and 0.35 ml of methyl iodide was added dropwise. The mixture was further stirred for 30 minutes at room temperature. Then, an aqueous solution of ammonium chloride (3 g/20 ml) was added, and the mixture was extracted with 20 ml of ether three times. The extract was washed with 30 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel; hexane and methylene chloride) to afford 1.125 g (yield 86%) of alpha-(p-tolylthio)-alpha-(m-phenoxyphenyl)propionitrile as a pale yellow oil.
Workup
- stirringThe mixture was further stirred for 30 minutes at room temperature
- extractionthe mixture was extracted with 20 ml of ether three times
- washThe extract was washed with 30 ml of water three times
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe oily residue was purified by column chromatography (silica gel; hexane and methylene chloride)
Sources & evidence
- ORD record
- ord-41e3db438f8244859a3e784bcced1f33
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04340740
Reaction notes
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