Sodium Hydroxide → HCID 67312828, Verbindung

To a solution of 2-chloro-3-(1-cyano-1-methylethyl)benzoic acid (1.98 g, 8.85 mmol) produced in Example A41(ii) in tetrahydrofuran (40 mL) were added oxalyl chloride (1.41 g, 11.1 mmol) and N,N-dimethylformamide (10 μL), and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in N,N-dimethylacetamide (40 mL). 4-Fluoro-3-(4-nitrophenoxy)aniline (4.69 g, 20.4 mmol) was added, and the mixture was stirred at room temperature for 14 hr. To the reaction mixture were added water (100 ml), 1N aqueous sodium hydroxide solution (50 mL) and ethyl acetate (200 mL). The organic layer was separated, washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give 2-chloro-3-(1-cyano-1-methylethyl)-N-[4-fluoro-3-(4-nitrophenoxy)phenyl]benzamide (2.01 g, 99%). The obtained compound was used in the next reaction without a further purification.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe obtained residue was dissolved in N,N-dimethylacetamide (40 mL)
3. stirringthe mixture was stirred at room temperature for 14 hr
4. customThe organic layer was separated
5. washwashed with saturated brine (10 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-c0ae00c39a3f442a9859edc602e948f7

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08324395B2