2,4-Dichloroaniline → Ethyl [4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

HRID 1398746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398746
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2[C:13]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:15]=[C:16]([Cl:17])[C:4]=2[N:3]=1.[Cl:23][C:24]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:25]=1[NH2:26].C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:17][C:16]1[C:4]2[N:3]=[C:2]([NH:26][C:25]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:24]=3[Cl:23])[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]=2[C:13]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 86632860Ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

Produkt 1

HCID 86632861Ethyl [4-chloro-2-[(2,4-dichlorophenyl)amino]-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetateAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (708 mg, 2.06 mmol), 2,4-dichloroaniline (1.00 g, 6.19 mmol) and N-methyl-2-pyrrolidinone (0.5 mL) was stirred at 100° C. for 3.5 days. After cooling, the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 3-15% ethyl acetate/n-hexane gradient mixture. The resulting solid was washed with n-hexane to give the title compound (115 mg, 0.245 mmol, 12%) as a colorless solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by basic silica gel column chromatography
  7. washeluting with a 3-15% ethyl acetate/n-hexane gradient mixture
  8. washThe resulting solid was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-12c9d1f3b5eb4d5db1418db53703dd3e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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