Reacción #1449

Ecuación de reacción

sodium hydride

water

6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

methyl iodide

→

6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

Disolventes

N,N-dimethylformamide

chloroform

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith cooling on an ice bath
2. 2
   workup.ADDITIONwas then added dropwise a solution
3. 3
   Otroprepared
4. 4
   workup.STIRRINGstirred for 24 hours at room temperature
5. 5
   Otrothe resulting organic layer was separated
6. 6
   Lavadowashed with a saturated sodium chloride aqueous solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   OtroAfter removing the solvent
9. 9
   workup.DISTILLATIONby distillation under a reduced pressure

Procedimiento

In a stream of argon, 144 mg of 60% sodium hydride was suspended in a small volume of N,N-dimethylformamide to which, with cooling on an ice bath, was then added dropwise a solution prepared by dissolving 500 mg of 6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine in 20 ml of N,N-dimethylformamide. After 1 hour of stirring at room temperature, the reaction solution was mixed with 0.11 ml of methyl iodide and stirred for 24 hours at room temperature. The reaction solution was mixed with water and chloroform, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography to obtain 351 mg of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine from the chloroform-methyl alcohol (30:1) eluate.

Fuente