Methyl iodide → HCID 10654914, compound

Temperature

70 °C

A flame-dried Schlenk flask under a nitrogen atmosphere was charged with sodium hydride (60% in mineral oil, 0.14 g, 3.5 mmol), 3-Methylsulfanyl-phenyl-cyanamide (0.493 g, 3.00 mmol) and anhydrous THF (5 ml). The mixture was stirred rapidly and heated to 70° C. for circa 0.5 hours. On cooling to room temperature, iodomethane (0.37 ml, 6.00 mmol) was added drop wise and the mixture stirred at room temperature over night. The resulting clear, colourless solution was concentrated under vacuum before water (30 ml) and diethylether (40 ml) were added. The organic phase was separated, dried over Na2SO4 and the diethylether solvent removed under vacuum to yield a crude residue. Purification by column chromatography on silica gel using dichloromethane as mobile phase afforded the title compound as a pale yellow oil (0.388 g, 73%).

1. temperatureOn cooling to room temperature
2. stirringthe mixture stirred at room temperature over night
3. concentrationThe resulting clear, colourless solution was concentrated under vacuum before water (30 ml) and diethylether (40 ml)
4. additionwere added
5. customThe organic phase was separated
6. dry with materialdried over Na2SO4
7. customthe diethylether solvent removed under vacuum
8. customto yield a crude residue
9. customPurification by column chromatography on silica gel

ORD record

ord-35b8fdc0937e4d6f9c2607a871338e8b

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058311B2