Reaktion #3679

Reaktionsgleichung

NaOH

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

triethylamine

2,5-dichlorobenzenesulfonyl chloride

2,5-dichlorobenzenesulfonyl chloride

triethylamine

→

solid

Ausbeute 177.6%

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

Ausbeute 177.6%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter another hour
2. 2
   workup.STIRRINGThe mixture is stirred at room temperature for 2 days
3. 3
   ExtraktionThe mixture is extracted with ethyl acetate
4. 4
   Waschenthe extract washed with 50% ammonium chloride solution, brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   SonstigeThe solvent is removed

Vorschrift

A mixture of 0.10 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.050 g of triethylamine and 0.083 g of 2,5-dichlorobenzenesulfonyl chloride in 2 ml of dichloromethane is stirred at room temperature for 1 hour and then 4 mg of 4-(N,N-dimethylamino)pyridine is added. After another hour, 93 mg of 2,5-dichlorobenzenesulfonyl chloride is added along with 50 mg of triethylamine. The mixture is stirred at room temperature for 2 days and 1N NaOH added. The mixture is extracted with ethyl acetate and the extract washed with 50% ammonium chloride solution, brine and dried (Na2SO4). The solvent is removed to give 0.30 g of solid. Trituration with ether-hexane gives 0.26 g of solid. This solid is dissolved in a mixture of 5 ml of tetrahydrofuran, 1 ml of methanol, 1 ml of 1N NaOH and the mixture stirred for 18 hours at room temperature. The organic solvents are removed and the mixture extracted with ether acetate. The extract is washed with NaHCO3, brine and dried (Na2 SO4). The solvent is removed and the residue (0.16 g) triturated with ether to give 0.14 g of yellow solid.

Quelle