Reacción #3676

Ecuación de reacción

2-chlorobenzenesulfonyl chloride

10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

triethylamine

→

white crystals

Rendimiento 20.9%

10-[4-[[(2-Chlorophenyl)sulfonyl]amino]benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Rendimiento 20.9%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine
2. 2
   Secadodried (Na2SO4)
3. 3
   FiltraciónThe solution is filtered through a thin pad of hydrous magnesium silicate
4. 4
   Concentraciónthe filtrate concentrated to dryness
5. 5
   OtroThe residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1)
6. 6
   Otroto give a solid
7. 7
   OtroCrystallization from ethyl acetate

Procedimiento

To a solution of 0,418 g of 2-chlorobenzenesulfonyl chloride in 5 ml of dichloromethane, cooled to 0° C. is added 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.346 μl of triethylamine. The mixture is stirred at room temperature overnight and diluted with 50 ml of dichloromethane. The mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1) to give a solid. Crystallization from ethyl acetate gives 0.165 g of white crystals, m.p. 206°-210° C.

Fuente