Sodium Hydroxide → Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate

HRID 2216699

Reaktionsgleichung

Reaktionsgleichung von HRID 2216699
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:20]1(/[CH:28]=[CH:29]/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1.C1C=CC2C(=NO[N+]=2[O-])C=1.[OH-].[Na+]>CO.C(#N)C.C(OCC)(=O)C>[CH:14]1([N:13]2[C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=3[N:1]=[C:26]2[C:23]2[CH:24]=[CH:25][C:20](/[CH:28]=[CH:29]/[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 68075BenzofuroxanHCID 4068248Ferrostatin-1HCID 53758764-Formyl-trans-stilbene

Produkt 1

HCID 10114855Ethyl 1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 3-amino-4-cyclohexylaminobenzoate (500 mg) obtained in Example 1, Step 3, was dissolved in methyl alcohol (6 ml) and trans-4-stilbenecarbaldehyde (397 mg) was added under ice-cooling. The mixture was stirred overnight at room temperature. The reaction mixture was ice-cooled and benzofuroxan (259 mg) dissolved in acetonitrile (2 ml) was added. The mixture was stirred for 7 hr at 50° C. The reaction mixture was ice-cooled. After 1N sodium hydroxide was added, ethyl acetate was added and the mixture was extracted. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1) to give the title compound (540 mg, yield 63%).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooled
  3. additionwas added
  4. stirringThe mixture was stirred for 7 hr at 50° C
  5. temperaturecooled
  6. extractionthe mixture was extracted
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel flash chromatography (developing solvent, n-hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-294c7be0f24a4fde8606a591f2753a0f
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112600B1

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