Hydrochloric Acid → Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethylamino-benzimidazole-7-carboxylate

HRID 1737882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1737882
CI.[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]2[C:29]([NH:30][C:31]([NH:33][CH2:34][CH3:35])=S)=[CH:28][CH:27]=[CH:26][C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][CH:12]=1)#[N:4].Cl>C(O)C>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:19]3[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=[CH:28][C:29]=3[N:30]=[C:31]2[NH:33][CH2:34][CH3:35])=[CH:13][CH:12]=1)#[N:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 53943039Ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate

Produkt 1

HCID 22596759Ethyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethylamino-benzimidazole-7-carboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl iodide (4.5 g) was added to a solution of ethyl 2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-(ethylthioureido)benzoate (1.8 g) in ethanol (50 ml), and the mixture was heated under reflux for 12 hours. To the reaction mixture was added 1N-HCl (60 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated to dryness and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and water and dried. The solvent was evaporated to dryness and the residue was purified by column chromatography on silica gel to afford yellow syrup (0.96 g, 58%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionthe concentrate was dissolved in ethyl acetate
  5. washThe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  6. customdried
  7. customThe solvent was evaporated to dryness
  8. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8d317203a2e04f9dba26a6635d03af2e
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962491

Notizen zur Reaktion

Wird geladen…