반응 #3584

반응 방정식

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

4-[(2-methylbenzoyl)amino]benzoyl chloride

triethylamine

→

residue

수율 131.1%

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

수율 131.1%

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   기타The cooling bath is removed and after about 30 minutes a complete solution
3. 3
   기타is obtained
4. 4
   workup.STIRRINGto stir at room temperature for 48 hours
5. 5
   농축the volatiles are concentrated in vacuo to a residue
6. 6
   workup.DISSOLUTIONThe residue is dissolved in 100 ml of ethyl acetate
7. 7
   세척washed with water, 2N citric acid, aqueous NaHCO3 and brine
8. 8
   건조The solution is dried with Na2SO4
9. 9
   농축the volatiles concentrated in vacuo

실험 절차

To a mixture of 1.93 g of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 15 ml of methylene chloride, cooled to 0° C. is added 1.13 ml of triethylamine. After stirring for 3 minutes, a mixture of 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 5 ml of methylene chloride is added. The cooling bath is removed and after about 30 minutes a complete solution is obtained. The reaction mixture is allowed to stir at room temperature for 48 hours and the volatiles are concentrated in vacuo to a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with water, 2N citric acid, aqueous NaHCO3 and brine. The solution is dried with Na2SO4 and the volatiles concentrated in vacuo to give 3.0 g of a residue. A 300 mg sample of the residue is purified by thick layer chromatography using 10% ethyl acetate-methylene chloride to give 160 mg of the desired product. The remainder of the crude material is purified by flash chromatography using 10% ethyl acetate in methylene chloride to give the desired product as a residue which is crystallized from ethyl acetate to give 800 mg of the desired product as white crystals, m.p. 212°-215° C.

출처