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

HRID 412362Notes

Reaction equation

HRID 412362 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-3789ad64238c4bd2a7a2c2c54d2c044c
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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