4-Toluenesulfonyl chloride → N-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-p-toluenesulfonamide

HRID 412339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 412339
Cl.Cl.[NH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][CH:5]=1.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.C(N(CC)CC)C>CN(C)C=O>[O:29]=[C:27]1[NH:26][C:25](=[O:30])[CH:24]([CH2:23][C:22]2[CH:31]=[CH:32][C:19]([O:18][CH2:17][C:15]3[N:14]([CH3:33])[C:13]4[CH:34]=[C:9]([O:8][C:7]5[CH:35]=[CH:36][C:4]([NH:3][S:43]([C:40]6[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=6)(=[O:45])=[O:44])=[CH:5][CH:6]=5)[CH:10]=[CH:11][C:12]=4[N:16]=3)=[CH:20][CH:21]=2)[S:28]1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Produkt 1

HCID 18537622N-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-p-toluenesulfonamideAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg), p-toluenesulfonyl chloride (153 mg), triethylamine (234 mg) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated and 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=2:1→4:1 as the eluant and the product was recrystallized from a mixture of ethyl acetate and diisopropyl ether to afford the title compound (237 mg, mp 132.0-135.6° C.).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate
  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
  7. customn-hexane=2:1→4:1 as the eluant and the product was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1dd652d900374ea09f7000ddf6cfb49f
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562849B1

Notizen zur Reaktion

Wird geladen…