Dimethylamine → 1-[3-(N,N-dimethylcarbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383971
[CH3:1][NH:2][CH3:3].Cl[C:5]([CH:7]([CH3:29])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]=[C:11]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:6]>CO>[CH3:1][N:2]([CH3:3])[C:5]([CH:7]([CH3:29])[CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:13]=2[N:12]=[C:11]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:6]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 211887451-[3-(Chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Produkt 1

HCID 211887871-[3-(N,N-dimethylcarbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In an dimethylamine (40% in water, 10 ml) was placed 1-[3-(chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (600 mg, 1.5 mmol). To this mixture 10 ml of methanol were added, to enhance solubility and the mixture was stirred for about 64 hours at room temperature. The reaction mixture was then concentrated under reduced pressure to produce 600 mg as a tan foam. The crude material was further purified by flash silica gel chromatography, eluting with a gradient solvent of 19:1 ethyl acetate:methanol to 9:1 ethyl acetate:methanol. The fractions containing the desired material were combined and concentrated in vacuo to yield 375 mg (63%) of the desired title compound as a white foam.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto produce 600 mg as a tan foam
  3. customThe crude material was further purified by flash silica gel chromatography
  4. washeluting with a gradient solvent of 19:1 ethyl acetate
  5. additionThe fractions containing the desired material
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ed3870bca52b4898b8501885a712ae65
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255494B1

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