Oxalyl chloride → 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide

Temperatur

0 °C

5-Cyano-2-methoxybenzoic-acid (0.73 g) obtained in step A, and 16 μL of N,N-dimethylformamide were dissolved in 18 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 0.54 mL of oxalyl chloride was added little by little, and the mixture was stirred for 2.7 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid. This solid was added, with the use of 10 mL of tetrahydrofuran, to a solution of 0.95 g of 4-trifluoromethoxy-2-chloroaniline and 2.1 mL of N,N-diisopropylethylamine dissolved in 20 mL of tetrahydrofuran. The mixture was stirred overnight at room temperature, and then tetrahydrofuran was distilled off under reduced pressure. The resulting solid was purified by silica gel column chromatography using methylene chloride as an elution solvent, thereby obtaining 1.37 g (90%) of 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide.

1. distillationThe reaction mixture was distilled under reduced pressure
2. customdried
3. customto obtain a light yellow solid
4. stirringThe mixture was stirred overnight at room temperature
5. distillationtetrahydrofuran was distilled off under reduced pressure
6. customThe resulting solid was purified by silica gel column chromatography

ORD-Eintrag

ord-13a52567c2bb4dabbffdb39581801e65

Quelldatensatz

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07705053B2