Potassium Cyanide → 1H-Benzimidazole-2-acetonitrile, 4,5,6,7-tetrahydro-

HRID 70794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 70794
[C-:1]#[N:2].[K+].Cl.Cl[CH2:6][C:7]1[NH:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[N:8]=1.C(=O)([O-])O.[Na+]>CCO>[NH:8]1[C:9]2[CH2:15][CH2:14][CH2:13][CH2:12][C:10]=2[N:11]=[C:7]1[CH2:6][C:1]#[N:2]

Komponenten

5

Edukt 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 136978322-(chloromethyl)-4,5,6,7-tetrahydro-1H-1,3-benzodiazole hydrochloride

Produkt 1

HCID 701702071H-Benzimidazole-2-acetonitrile, 4,5,6,7-tetrahydro-Ausbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

An aqueous solution (30 ml) of potassium cyanide (15 g) was ice-cooled, then, an EtOH (140 ml) solution of 2-(chloromethyl)-4,5,6,7-tetrahydro-1H-benzimidazole hydrochloride (12.0 g) was added, and stirring was performed at room temperature for 1 hour and then at 50° C. for 1, hour. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction liquid, followed by concentration under reduced pressure and extraction with chloroform. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (28% aqueous ammonia/methanol/chloroform) to obtain 4,5,6,7-tetrahydro-1H-benzimidazol-2-yl acetonitrile (8.6 g).

Aufarbeitung

  1. temperaturecooled
  2. customat 50° C.
  3. concentrationfollowed by concentration under reduced pressure and extraction with chloroform
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (28% aqueous ammonia/methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-5ad1a409f8ef42a49924cb83dd1a128b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822688B2

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