Reaction #3660

Reaction equation

10,11-dihydro-10-(3-methyl-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

2,4-dichlorobenzoyl chloride

diisopropylethylamine

→

crystals

Yield 84.1%

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

Yield 84.1%

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe mixture is washed with water
2. 2
   Dryingdried (MgSO4)
3. 3
   ConcentrationThe filtrate is concentrated
4. 4
   workup.ADDITIONhexane added
5. 5
   Otherto give crystals
6. 6
   OtherRecrystallization from dichloromethane-hexane

Procedure

A mixture of 0.40 g of 10,11-dihydro-10-(3-methyl-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.40 g of 2,4-dichlorobenzoyl chloride and 0.75 g of diisopropylethylamine in 50 ml of dichloromethane is stirred at room temperature for 16 hours. The mixture is washed with water, dried (MgSO4) and the solution passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and hexane added to give crystals. Recrystallization from dichloromethane-hexane gives 0.52 g of crystals, m.p. 213°-215° C.

Source