Ammonium Hydroxide → 1-[3-(Carbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

HRID 1383970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383970
[OH-].[NH4+:2].Cl[C:4]([CH:6]([CH3:28])[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=2[N:11]=[C:10]1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:5]>CO>[C:4]([CH:6]([CH3:28])[CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=2[N:11]=[C:10]1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)(=[O:5])[NH2:2]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 211887451-[3-(Chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Produkt 1

HCID 211885801-[3-(Carbamoyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazoleAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In an ammonium hydroxide solution (28%, 10 ml) was placed 1-[3-(chlorocarbonyl)butyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (400 mg, 1.0 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 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 300 mg (73%) of the desired title compound as a white foam.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto produce 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-90860ef74b6c4ef8b941c01bf9cf6dd0
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255494B1

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