Methyl iodide → HCID 25264103, compound

Temperature

60 °C

Methanol (25 mL) was added to a mixture of methyl isothiocyanate (1.052 g, 14.4 mmol) and 5-methylpyrazine-2-carbohydrazide (2.192 g, 14.4 mmol). The resulting mixture was heated at 60° C. for 1 h, and concentrated in vacuo. The residue was dissolved in aqueous sodium hydroxide solution (0.8M, 20 mL, 16 mmol) and the resulting solution was heated at 60° C. for 19 h, then cooled to room temperature. Aq. NaOH (6M, 2.6 mL, 15.6 mmol) was added followed by iodomethane (1.24 mL, 19.8 mmol) in ethanol (31 mL) plus additional water (5 mL rinse) and the resulting mixture was stirred 1 hour at room temperature. The product was partitioned between water (added 30 mL) and dichloromethane (300 mL). The aqueous layer was extracted with dichloromethane (4×100 mL). The combined organic layers were washed with water (75 mL) and brine (75 mL) and dried over sodium sulfate. Removal of the solvent in vacuo followed by flash chromatography (silica gel, 2-3% methanol in dichloromethane) yielded the title compound (2.559 g, 80%).

1. concentrationconcentrated in vacuo
2. temperaturethe resulting solution was heated at 60° C. for 19 h
3. temperaturecooled to room temperature
4. customThe product was partitioned between water (added 30 mL) and dichloromethane (300 mL)
5. extractionThe aqueous layer was extracted with dichloromethane (4×100 mL)
6. washThe combined organic layers were washed with water (75 mL) and brine (75 mL)
7. dry with materialdried over sodium sulfate
8. customRemoval of the solvent in vacuo

ORD record

ord-61db73aebfd14195ae4fa98df3c9c540

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960422B2