Reaction #3692

Reaction equation

chloroacetyl chloride

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

triethylamine

→

beige solid

Yield 100.1%

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

Yield 100.1%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Otherthen partitioned with 10 ml of 50% NaHCO3
2. 2
   Otherthe methylene chloride evaporated in vacuo
3. 3
   FiltrationThe remaining suspension is filtered
4. 4
   Washwashed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml)
5. 5
   Otherdried in vacuo

Procedure

To a stirred solution of 0.91 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]-benzodiazepine in 10 ml of methylene chloride is added 0.46 g of triethylamine and 36 mg of dimethylaminopyridine followed by the slow addition of 0.42 g of chloroacetyl chloride in 5 ml of methylene chloride. The resulting mixture is stirred at room temperature for 3 hours then partitioned with 10 ml of 50% NaHCO3 and the methylene chloride evaporated in vacuo. The remaining suspension is filtered, washed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml) and dried in vacuo to give 1.14 g of beige solid. MS(CI): 380(M+H).

Source