Sodium Bicarbonate → 2-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 349477

Reaktionsgleichung

Reaktionsgleichung von HRID 349477
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH:12][C:13](=[N:22]Cl)[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[CH:5]=1.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3]([C:4]1[C:5]2[N:22]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[NH:12][C:6]=2[C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)=[O:24]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 691197333-[(2,4-dichloro-N-chloro-benzimidoyl)-amino]-4-methoxy-benzoic acid methyl ester

Produkt 1

HCID 691199112-(2,4-dichloro-phenyl)-7-methoxy-1H-benzoimidazole-4-carboxylic acid methyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-[(2,4-dichloro-N-chloro-benzimidoyl)-amino]-4-methoxy-benzoic acid methyl ester (4 g, 10.32 mmol) obtained in step 1 was dissolved in 50 ml of 50% methanol and NaHCO3 (2.19 g, 20.64 mmol) was added dropwise thereto at room temperature and refluxed for 5 min. The resulting solution was cooled to room temperature, extracted with ethyl acetate, and the extract was concentrated under a reduced pressure. The resulting residue was purified by recrystallization from ethyl acetate/hexane to obtain the title compound (3.2 g, 5.47 mmol) in a yield of 88%.

Aufarbeitung

  1. temperatureThe resulting solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationthe extract was concentrated under a reduced pressure
  4. customThe resulting residue was purified by recrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-29de0b7634914a24a09ea761300e60c2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179832B2

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