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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 412350Erstellt: 25. Oktober 2026

Hydrochloric Acid → 1-[2-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]urea hydrochloride

https://huagongshe.com/reaction/412350

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktHydrochloric AcidHCID 313—
EduktTriethylamineHCID 8471—
Edukt4-(Trifluoromethyl)phenyl isocyanateHCID 73768—
Edukt5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochlorideHCID 86587773—
LösungsmittelDiethyl EtherHCID 3283—
LösungsmittelDimethylformamideHCID 6228—
LösungsmittelTetrahydrofuranHCID 8028—
Lösungsmittel1,4-DioxaneHCID 31275—
Produkt1-[2-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]urea hydrochlorideHCID 1853756679,7%

Reaktionsschritte

1-[2-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)ethyl]-3-(4-trifluoromethylphenyl)urea hydrochloride was obtained by a similar procedure to that described in Example 31 using 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.3 g), α,α,α-trifluoro-p-tolyl isocyanate (97 mg), triethylamine (65 mg) and anhydrous N,N-dimethylformamide (5 ml). To a solution of the product in tetrahydrofuran (10 ml) was added 4N hydrogen chloride in 1,4-dioxane (10 ml) and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added diethyl ether (50 ml) and this mixture was further stirred for 30 minutes. The precipitate was isolated by filtration and washed with ethyl acetate to afford the title compound (0.3 g, mp 153-156° C.).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06562849B1
Quelldatensatzuspto-grants-2003_05
ORD IDord-3523880492f942cda65b0e750a510951
Quellennotizuspto-grants-2003_05