Reacción #499511

Ecuación de reacción

5-[4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

4-chlorophenyl isothiocyanate

triethylamine

→

title compound

Rendimiento 63.9%

1-(4-Chlorophenyl)-3-(4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]-2,6-dimethylphenyl)thiourea

Rendimiento 63.9%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with water
3. 3
   OtroThe precipitate was isolated by filtration
4. 4
   Otrochromatographed on a silica gel column

Procedimiento

A mixture of 5-[4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (288 mg), 4-chlorophenyl isothiocyanate (102 mg), triethylamine (121 mg) and anhydrous tetrahydrofuran (10 ml) was stirred at room temperature for 23 hours. The reaction mixture was concentrated and diluted with water. The precipitate was isolated by filtration and then chromatographed on a silica gel column using ethyl acetate:n-hexane=3:1 as the eluant to afford the title compound (215 mg, mp 160-162° C.).

Fuente