Reaction #3588

Reaction equation

2-chlorobenzoyl chloride

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

→

desired product

Yield 72.1%

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

Yield 72.1%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherThe bath is removed
2. 2
   workup.STIRRINGthe reaction mixture stirred at room temperature for 18 hours
3. 3
   ConcentrationThe volatiles are concentrated in vacuo
4. 4
   Otherto give a residue which
5. 5
   Washwashed with water, 2N citric acid, 1M NaHCO3 and brine
6. 6
   DryingThe organic layer is dried with Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Otherto give a residue which
10. 10
    Otheris crystallized from methylene chloride

Procedure

To a solution of 347 mg of 2-chlorobenzoyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamineo 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 methylene chloride, 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 methylene chloride to give 525 mg of the desired product as a white crystalline solid, m.p. 228°-230° C.

Source