Ammonium Chloride → HCID 66777794, Verbindung

To a solution (100 mL) of 6-methoxy-1-methyl-1H-benzoimidazole (4.07 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added a 1.6M solution (30.1 mL) of n-butyllithium in hexane at −78° C., and the mixture was stirred under nitrogen atmosphere for 30 min. A solution (50 mL) of N-methoxy-N-methylcyclohexanecarboxamide (5.15 g) synthesized in the above-mentioned (3) in tetrahydrofuran was added, and the mixture was stirred at −78° C. for 1 hr and at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether=1:5, volume ratio) to give the title object compound (5.80 g, 85%) as white crystals.

1. additionwas added
2. stirringthe mixture was stirred at −78° C. for 1 hr and at room temperature for 2 hr
3. customto quench
4. customthe reaction
5. extractionthe reaction mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether=1:5, volume ratio)

ORD-Eintrag

ord-8991033417c74fcc957ceb8d77928c4b

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08436043B2