Butylamine → 2-Butylaminomethylbenzimidazole

HRID 1071452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071452
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].Cl[CH2:7][C:8]1[NH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1>C(#N)C.CN(C)C=O>[CH2:1]([NH:5][CH2:7][C:8]1[NH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 2

HCID 8007ButylamineHCID 785712-Chloromethylbenzimidazole

Produkt 1

HCID 131694082-ButylaminomethylbenzimidazoleAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Butylamine (30 mL, 300 mmol) was dissolved in 150 mL of acetonitrile at room temperature. 2-Chloromethylbenzimidazole (5 g, 30 mmol) dissolved in 50 mL dimethylformamide was added dropwise. After stirring 3 hours at room temperature, the solvent was removed in vacuo. The residue was dissolved in 100 mL ethyl acetate and washed 2×100 mL H2O followed by 1×100 mL brine. The organic layer was dried over MgSO4, filtered, and then concentrated. The residue was purified by silica gel chromatography eluting first with ethyl acetate then with 10/2/1 ethyl acetate/methanol/triethylamine to yield 2.6 g 2-butylaminomethylbenzimidazole.

Aufarbeitung

  1. additionwas added dropwise
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 100 mL ethyl acetate
  4. washwashed 2×100 mL H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting first with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fdcaa435a4ac4013b98d22112ea800a7
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906075B2

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