Reacción #3597

Ecuación de reacción

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

N-chlorosuccinimide

→

desired product

Rendimiento 68.8%

N-[4-(3-Chloro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)ylcarbonyl)phenyl]-2-methylbenzamide

Rendimiento 68.8%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe bath is removed
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITcontinued for 2.25 hours
4. 4
   workup.ADDITIONThe reaction mixture is added to ice-water
5. 5
   Extracciónextracted with ether
6. 6
   OtroThe organic layer is dried
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto give a foam which
9. 9
   Otrois crystallized from ethyl acetate-hexane

Procedimiento

To an ice-water cooled suspension of 211 mg of 2-methyl-N-[4-(5H-pyrrolo[2,1-c][1,4]-benzodiazepin-10(11H)-ylcarbonyl)-phenyl]benzamide in 5 ml of tetrahydrofuran is added 67 mg of N-chlorosuccinimide followed by continued stirring in the cold for 10 minutes. The bath is removed and stirring continued for 2.25 hours. The reaction mixture is added to ice-water and extracted with ether. The organic layer is dried and concentrated in vacuo to give a foam which is crystallized from ethyl acetate-hexane to give 157 mg of the desired product as an orange-pink solid, m.p. 185°-187° C.

Fuente