Acetyl chloride → 5-{4-[6-(4-Acetylaminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

HRID 412362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412362
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].Cl.Cl.[NH2:14][C:15]1[CH:47]=[CH:46][C:18]([O:19][C:20]2[CH:21]=[CH:22][C:23]3[N:27]=[C:26]([CH2:28][O:29][C:30]4[CH:43]=[CH:42][C:33]([CH2:34][CH:35]5[S:39][C:38](=[O:40])[NH:37][C:36]5=[O:41])=[CH:32][CH:31]=4)[N:25]([CH3:44])[C:24]=3[CH:45]=2)=[CH:17][CH:16]=1>CN(C)C=O>[O:40]=[C:38]1[NH:37][C:36](=[O:41])[CH:35]([CH2:34][C:33]2[CH:42]=[CH:43][C:30]([O:29][CH2:28][C:26]3[N:25]([CH3:44])[C:24]4[CH:45]=[C:20]([O:19][C:18]5[CH:46]=[CH:47][C:15]([NH:14][C:8](=[O:10])[CH3:9])=[CH:16][CH:17]=5)[CH:21]=[CH:22][C:23]=4[N:27]=3)=[CH:31][CH:32]=2)[S:39]1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Produkt 1

HCID 98065795-{4-[6-(4-Acetylaminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (0.36 ml) and acetyl chloride (0.06 ml) were added to a solution of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) in anhydrous N,N-dimethylformamide (8 ml) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=4:1→1:0→ethyl acetate:methanol=10:1 as the eluant to afford the title compound (320 mg, white amorphous, mp 92-95° C.).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-3789ad64238c4bd2a7a2c2c54d2c044c
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

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