Reaktion #3587

Reaktionsgleichung

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

2,4-dichlorobenzoyl chloride

triethylamine

→

desired product

Ausbeute 53.5%

N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide

Ausbeute 53.5%

Lösungsmittel

ethyl acetate

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe bath is removed
2. 2
   workup.STIRRINGthe reaction mixture stirred at room temperature for 18 hours
3. 3
   EinengenThe volatiles are concentrated in vacuo
4. 4
   Sonstigeto give a residue which
5. 5
   Waschenwashed with water, 2N citric acid, 1M NaHCO3 and brine
6. 6
   TrocknenThe organic layer is dried with Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto give a residue which
10. 10
    Sonstigeis crystallized from ethyl acetate

Vorschrift

To a solution of 415 mg of 2,4-dichlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 18 hours. The volatiles are concentrated in vacuo to give a residue which is dissolved in ethyl acetate, washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried with Na2SO4, filtered and concentrated in vacuo to give a residue which is crystallized from ethyl acetate to give 420 mg of the desired product as a crystalline solid, m.p., 210°-212° C.

Quelle