تفاعل #3701

معادلة التفاعل

2,4-dichlorobenzoyl chloride

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

sodium hydride

→

tan foam

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

المذيبات

dioxane

dioxane

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwarmed slightly
2. 2
   أخرىto obtain a nearly complete solution
3. 3
   درجة الحرارةThe mixture is warmed slightly
4. 4
   workup.WAITGas evolution stops in a few minutes
5. 5
   درجة الحرارةThe reaction mixture is cooled to room temperature
6. 6
   أخرىThe volatiles are evaporated in vacuo to a residue which
7. 7
   أخرىis partitioned between water and chloroform
8. 8
   أخرىThe organic layer is separated
9. 9
   استخلاصthe aqueous phase extracted with chloroform two more times
10. 10
    ترشيحfiltered through MgSO4
11. 11
    أخرىThe filtrate is evaporated in vacuo to a tan foam which
12. 12
    أخرىis purified by flash chromatography on silica gel by elution with CHCl3 and 3-7% CH3 OH in chloroform

الإجراء التجريبي

A slurry of 0.330 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 15 ml of dioxane is stirred and warmed slightly to obtain a nearly complete solution. The reaction mixture is cooled to room temperature and 43 mg of sodium hydride in oil added. The mixture is warmed slightly. Gas evolution stops in a few minutes. The reaction mixture is cooled to room temperature and 153 μl of 2,4-dichlorobenzoyl chloride in 2.5 ml of dioxane added. An additional 3.5 ml of dioxane is added and the reaction mixture stirred at room temperature for 2 days. The volatiles are evaporated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is separated and the aqueous phase extracted with chloroform two more times. The combined organic layers are trated with activated carbon and filtered through MgSO4. The filtrate is evaporated in vacuo to a tan foam which is purified by flash chromatography on silica gel by elution with CHCl3 and 3-7% CH3 OH in chloroform to give 310 mg of tan foam.

المصدر