Ammonium Chloride → HCID 86670260, compound

Temperature

0 °C

In a dehydrated tetrahydrofuran (35 ml) solution of N-(4-chloro-phenyl)-thioacetamide (3.3 g), 27 ml of n-butyllithium (1.59 mol/l, n-hexane solution) was added dropwise at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 1 hour, the mixture was cooled to −78° C. A tetrahydrofuran (35 ml) solution of 5-bromo-2-methyl-2-pentene (2.9 g) was added dropwise thereto. After raising the temperature to room temperature and further stirring for 30 minutes, an aqueous saturated ammonium chloride solution was added and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.0 g of the target compound.

1. temperaturethe mixture was cooled to −78° C
2. temperatureAfter raising the temperature to room temperature
3. stirringfurther stirring for 30 minutes
4. extractionthe reaction mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated saline solution
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-c05cebd646944122ad3ccdadfa8d6c8c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012493B2