Dimethyl Sulfoxide → 5-Pentylbenzimidazol-2-one

HRID 2233544

Reaktionsgleichung

Reaktionsgleichung von HRID 2233544
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1.[O-]CC.[Na+].CS(C)=O.Br[CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH2:1]([C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1)[CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8002Butyl bromideHCID 2723922Sodium ethoxideHCID 200643865-Methylbenzimidazol-2-one

Produkt 1

HCID 671748435-Pentylbenzimidazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of 5-methylbenzimidazol-2-one (50 mg, 3.378×10−4 mol) in dry ethanol (5 ml), the freshly made sodium ethoxide in ethanol (1M, 1.01×10−3 mol equivalents) was added dropwise under a nitrogen atmosphere. At room temperature the mixture was stirred for 3 hrs under an atmosphere of nitrogen and the ethanol was then removed under reduced pressure. To this a solution of dry DMSO (3 ml) and 1-bromobutane (54 μl, 5.1×10−4 mol) was added and stirred at room temperature under an atmosphere of nitrogen overnight. The reaction mixture was then quenched with ice and neutralised using 1M hydrochloric acid solution, forming a white solid product. The solid was collected by filtration and purified using preparative thin liquid chromatography with 10% MeOH/CHCl3.

Aufarbeitung

  1. customthe ethanol was then removed under reduced pressure
  2. stirringstirred at room temperature under an atmosphere of nitrogen overnight
  3. customThe reaction mixture was then quenched with ice
  4. customforming a white solid product
  5. filtrationThe solid was collected by filtration
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-54938d4a31ba44f994559747aa8c38a1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709514B2

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