Reaction #83509

Reaction equation

(±)-2-chloro-2-phenylacetyl chloride

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

triethylamine

→

pink solid

Yield 106.9%

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

Yield 106.9%

Solvents

NaHCO3

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherThe methylene chloride is evaporated
2. 2
   Extractionthe residue is extracted with ethyl acetate
3. 3
   WashThe separated organic layer is washed with saturated NaHCO3 and brine
4. 4
   Dryingdried with Na2SO4
5. 5
   Filtrationby filtering through a pad of hydrous magnesium silicate
6. 6
   OtherThe filtrate is evaporated to a residue which
7. 7
   workup.STIRRINGis stirred with etherhexane

Procedure

To a solution of 0.61 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.47 g of (±)-2-chloro-2-phenylacetyl chloride in 2 ml of methylene chloride. The mixture is stirred at room temperature for 1 hour and then diluted with 10 ml of 50% NaHCO3. The methylene chloride is evaporated and the residue is extracted with ethyl acetate. The separated organic layer is washed with saturated NaHCO3 and brine and then dried with Na2SO4 followed by filtering through a pad of hydrous magnesium silicate. The filtrate is evaporated to a residue which is stirred with etherhexane to give 0.98 g of pink solid. MS(CI): 456(M+H).

Source