p-Toluenesulfonic acid → 3-[(2,4-dichloro-N-chloro-benzimidoyl)-amino]-4-methoxy-benzoic acid methyl ester

Temperatur

180 °C

Anhydrous p-toluene sulfonic acid (20.99 g, 110.04 mmol) was melted at 120° C. and 3-amino-4-methoxy benzoic acid methyl ester (10 g, 55.20 mmol) obtained in step 1 of Preparation Example 1 and 2,4-dichlorobenzonitrile (18.99 g, 110.04 mol) were added thereto and stirred at 180° C. for 6 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The concentrate was dissolved in 50% methanol and 5% NaOCl (30 ml, 20.64 mmol) was added dropwise thereto. After 5 min, the resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent—MeOH:CDCl3=5:95, Merck, Silicagel 60) to obtain the title compound (18 g, 10.32 mmol) in a yield of 84%.

1. additionwere added
2. temperatureThe resulting solution was cooled to room temperature
3. extractionThe resulting mixture was extracted with ethyl acetate
4. dry with materialthe extract was dried over MgSO4
5. concentrationconcentrated under a reduced pressure
6. dissolutionThe concentrate was dissolved in 50% methanol
7. waitAfter 5 min
8. extractionthe resulting mixture was extracted with ethyl acetate
9. dry with materialthe extract was dried over MgSO4
10. concentrationconcentrated under a reduced pressure
11. customThe resulting residue was purified by silica gel column chromatography (eluent—MeOH:CDCl3=5:95, Merck, Silicagel 60)

ORD-Eintrag

ord-3577b128423d43f1b30b6d9e0ebc0a93

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07179832B2