Reaktion #3584

Reaktionsgleichung

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

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

triethylamine

→

residue

Ausbeute 131.1%

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

Ausbeute 131.1%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle