Dichloromethane → HCID 73794030, compound

1.78 Grams of methyl methylthiomethyl sulfoxide was dissolved in 20 ml of THF, and to which 375 mg of sodium hydride was added under cooling with ice, followed by 30 minutes' stirring at room temperature. Thereafter 1.6 ml of isobutyronitrile was added and stirred for 16 hours at room temperature, and for 6 hours at 50°C., followed by further addition of 70 ml of methylene chloride and 2 ml of water, and subsequent an hour's stirring at room temperature. The reaction mixture was dried with Glauber's salt, and concentrated under reduced pressure to leave a yellow solid. Washing the solid with a carbon tetrachloride-n-hexane system, 1.525 g of 1-methylsulfinyl-1-methylthio-2-amino-3-methyl-1-butene was obtained as a light yellow solid. The washing was concentrated under reduced pressure, and subjected to a column chromatography (silica gel, methylene chloride, ethyl acetate, and methanol) to allow the recovery of 117 mg of methyl methylthiomethyl sulfoxide and 480 mg of 1-methylsulfinyl-1-methylthio-2-amino- 3-methyl-1-butene. The isolation yield was 72.3%, and the conversion yield was 77.5%.

1. temperatureunder cooling with ice
2. stirringstirred for 16 hours at room temperature
3. waitfor 6 hours at 50°C.
4. stirringstirring at room temperature
5. dry with materialThe reaction mixture was dried with Glauber's salt
6. concentrationconcentrated under reduced pressure
7. customto leave a yellow solid
8. washWashing the solid with a carbon tetrachloride-n-hexane system

ORD record

ord-2750bc027b2a46fe92e6b8342072c39a

Source dataset

uspto-grants-1976_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03952044