Methyl chloroformate → HCID 58355341, compound

Temperature

-15 °C

1-(4-Methoxybutyl)-4,5,6,7-tetrahydro-1H-benzimidazole (625 mg) was dissolved in acetonitrile (5 ml), and the mixture was cooled to −15° C. Triethylamine (1.25 ml) and methyl chlorocarbonate (691 μl) were added dropwise. The reaction mixture was heated to room temperature and stirred for 12 hr. The reaction mixture was again cooled to −15° C., triethylamine (1.25 ml) and methyl chlorocarbonate (691 μl) were added dropwise, heated to room temperature and stirred for 12 hr. This operation was further repeated 3 times, aqueous sodium bicarbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (225 mg).

1. temperatureThe reaction mixture was heated to room temperature
2. temperatureThe reaction mixture was again cooled to −15° C.
3. temperatureheated to room temperature
4. stirringstirred for 12 hr
5. additionwas added to the reaction mixture
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was evaporated under reduced pressure
10. washa fraction eluted with ethyl acetate
11. concentrationwas concentrated under reduced pressure

ORD record

ord-fb9b40afa72a40e19b8b98f85c2b76ed

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221836B2