StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

5-Aminobenzimidazole → HCID 178441338, Verbindung

HRID 706266
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 706266
Cl[C:2](OC1C=CC=CC=1)=[O:3].[NH2:11][C:12]1[CH:20]=[CH:19][C:15]2[N:16]=[CH:17][NH:18][C:14]=2[CH:13]=1.[NH2:21][CH2:22][C:23](=O)[C:24]([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[C:24]([CH:23]1[N:11]([C:12]2[CH:20]=[CH:19][C:15]3[NH:16][CH:17]=[N:18][C:14]=3[CH:13]=2)[C:2](=[O:3])[NH:21][CH2:22]1)([CH3:27])([CH3:26])[CH3:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 136235-AminobenzimidazoleHCID 15891Phenyl chloroformateHCID 4266281-Amino-3,3-dimethylbutan-2-one

Produkt 1

HCID 178441338HCID 178441338, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound was synthesized as hydrochloride salt by the following procedure. Phenyl chloroformate (0.98 mL, 7.8 mmol) was dissolved in CH2Cl2, cooled down to 0° C. and 5-aminobenzimidazole (0.865 g, 6.5 mmol) was added slowly. The mixture was kept at 0° C. for 30 min and then the mixture was allowed to adapt ambient temperature. The mixture was stirred at ambient temperature for 2 h. The resulting solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution, 1-amino-3,3-dimethylbutan-2-one (0.986, 6.5 mmol) and TEA (2.73 mL, 19.5 mmol) were added. The mixture was kept at 40° C. for 2 h. The solvent was removed and purified by means of preparative HPLC. The remains were re-dissolved in MeOH and a small amount of HCl was added (1-2%). The solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60° C.) for 4 h. The catalyst was removed by filtration through a pad of CELITE® and the residue was washed with water. The organic layer was dried, filtrated and the solvent was removed to result in the final product.

Aufarbeitung

  1. customto adapt ambient temperature
  2. customThe resulting solid was withdrawn by suction
  3. customdried
  4. waitThe mixture was kept at 40° C. for 2 h
  5. customThe solvent was removed
  6. custompurified by means of preparative HPLC
  7. dissolutionThe remains were re-dissolved in MeOH
  8. additiona small amount of HCl was added (1-2%)
  9. waitThe solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60° C.) for 4 h
  10. customThe catalyst was removed by filtration through a pad of CELITE®
  11. washthe residue was washed with water
  12. customThe organic layer was dried
  13. filtrationfiltrated
  14. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-e2d64cf0ca5e4ed5b703cc3244a8359f
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09173885B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion