Sodium hydride → 2-Butyl 4-methyl-1-[(4-nitrophenyl)methyl]-1H-benzimidazole

HRID 5021

Reaktionsgleichung

Reaktionsgleichung von HRID 5021
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:4][CH2:5][CH3:6].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>CN(C=O)C>[CH2:3]([C:7]1[N:11]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:9]=2[N:8]=1)[CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 178418620HCID 178418620, Verbindung

Produkt 1

HCID 197975362-Butyl 4-methyl-1-[(4-nitrophenyl)methyl]-1H-benzimidazoleAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a slurry of NaH (60%, 0.21 g. 5.3 mmol) in DMF was added with stirring a solution of 2-butyl-4-methyl-benzimidazole (1 g. 5.3 mmol) in DMF (20 mL under nitrogen atmosphere. After the gas evolution was complete, the reaction mixture was cooled in ice and a solution of 4-nitrobenzyl bromide (1.5 g, 5.3 mmol) in DMF (5 mL) was added with stirring. The reaction mixture was allowed to warm up slowly to room temperature and stirred for 16 hours. DMF was distilled under reduced pressure and the residue was taken up in EtOAc, and the solution was washed with water. It was dried over MgSO4 and evaporated to give a solid which was chromatographed (CH2Cl2 /EtOAc 4/1-EtOAc) to give 1.5 g of a solid, MP 115°-116° C.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled in ice
  2. stirringstirred for 16 hours
  3. distillationDMF was distilled under reduced pressure
  4. washthe solution was washed with water
  5. dry with materialIt was dried over MgSO4
  6. customevaporated
  7. customto give a solid which
  8. customwas chromatographed (CH2Cl2 /EtOAc 4/1-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8b03c4b147cc4e73961cfb46cd3fddcd
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242939

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