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Ethyl Acetate → (E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile

HRID 452144
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 452144
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[NH:9][C:8]([CH2:10][CH2:11][CH3:12])=[N:7][C:6]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:40]=[CH:39][C:26]2/[C:27](=[CH:36]/[C:37]#[N:38])/[C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[CH2:30][CH2:31][C:25]=2[CH:24]=1.C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH3:12])[N:7]([CH2:22][C:23]3[CH:40]=[CH:39][C:26]4/[C:27](=[CH:36]/[C:37]#[N:38])/[C:28]5[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=5[CH2:30][CH2:31][C:25]=4[CH:24]=3)[C:6]=2[CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67210773(E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrileHCID 178439846HCID 178439846, Verbindung

Produkt 1

HCID 67210768(E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile
Ausbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

[step 1] Under a nitrogen atmosphere, 6-bromo-4-methyl-2-propylbenzimidazole (WO2004082621; 300 mg, 1.19 mmol) was dissolved in DMF (3 mL), and the mixture was cooled to 0° C. Potassium carbonate (829 mg, 6.00 mmol) was added, and the mixture was stirred at room temperature for 20 min. To this mixture was added (E)-2-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (421 mg, 1.30 mmol) obtained in Reference Example B1, and the mixture was stirred at room temperature for 4 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/3) to give (E)-[2-(6-bromo-4-methyl-2-propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (615 mg, 95%).

Aufarbeitung

  1. customobtained in Reference Example B1
  2. stirringthe mixture was stirred at room temperature for 4 hr
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/3)

Quellen und Nachweise

ORD-Eintrag
ord-0f25278f54a848e49ce1d340ae9eaeee
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486980B2

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