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

Benzimidazole → 1-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole

HRID 2268506
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268506
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH3:16][O:15][C:14]1[C:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[CH:24]3)[CH2:10][CH2:9][C:8]=2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=1[O:17][CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 5798BenzimidazoleHCID 10340Sodium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

Produkt 1

HCID 183485591-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazoleAusbeute 32,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.50 g), benzimidazole (443 mg), and sodium carbonate (760 mg) in DMF (15 ml) was stirred at 70° C. for 8 hr. The reaction mixture was diluted with water and extracted with combined solution of ethyl acetate and THF. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was diluted with diethylether and the resultant crystals were removed by filtration. The filtrate was concentrate in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2) and then with recrystallization from hexane-ethyl acetate to obtain the entitled compound (480 mg).

Aufarbeitung

  1. extractionextracted with combined solution of ethyl acetate and THF
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted with diethylether
  6. customthe resultant crystals were removed by filtration
  7. concentrationThe filtrate was concentrate in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2)
  9. customwith recrystallization from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ad73347caa454111b59c1ad69d1b0a9c
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion