Reacción #81613

Ecuación de reacción

hydrochloric acid

3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid

sodium methanesulphinate

sodium methanesulphinate

→

title compound

Rendimiento 41.0%

3-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-(4-methylsulphonylbenzoyl)benzenepropanoic acid

Rendimiento 41.0%

Disolventes

dimethylsulphoxide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheating
2. 2
   Extracciónextracted several times with ethyl acetate
3. 3
   LavadoThe combined extracts were washed with water
4. 4
   Secadodried (MgSO4)
5. 5
   Otroevaporated
6. 6
   OtroThe residue was chromatographed on silica gel
7. 7
   Otroevaporated

Procedimiento

A solution of 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-(4-fluorobenzoyl)benzenepropanoic acid (0.25 g) and sodium methanesulphinate (0.61 g) in dimethylsulphoxide (1.0 ml) was heated at 130° C. under dry nitrogen for 30 hours. Additional sodium methanesulphinate (1.2 g) was added and heating was continued for a further 20 hours. The solution was diluted with water, acidified with 2N hydrochloric acid and extracted several times with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel using dichloromethane/methanol (97:3) as eluent. The product fractions were combined and evaporated to give the title compound as a foam (0.115 g), Rf 0.25(SS 8). Found: C,54.96; H,4.53; N,2.18. C25H24CINO7S2 requires: C,54.59; H,4.40; N,2.55%.

Fuente