Reaction #83497

Reaction equation

2-chlorobenzenesulfonyl chloride

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

triethylamine

→

white crystals

Yield 20.9%

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

Yield 20.9%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

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

Procedure

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.

Source