Reacción #1563891

ord-270ea86498a74b5889390c8f103fb76a

Ecuación de reacción

BrCCNCCBr
bis(2-bromoethyl)amine
COc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc([N+](=O)[O-])cc1
Compound 25
COc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc([N+](=O)[O-])cc1
2-amino-N-(2-methoxyphenyl)-6-(4-nitrophenylthi-o)benzamide
[Na+].[OH-]
NaOH
COc1ccccc1NC(=O)c1c(Sc2ccc([N+](=O)[O-])cc2)cccc1N1CCNCC1
solid
Rendimiento 82.0%
COc1ccccc1NC(=O)c1c(Sc2ccc([N+](=O)[O-])cc2)cccc1N1CCNCC1
N-(2-methoxyphenyl)-2-((4-nitrophenyl)thio)-6-(piperazinyl)benzamide
Rendimiento 82.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto get crude product
  2. 2
    FiltraciónThe crude solid was filtered
  3. 3
    Lavadowashed several times with water
  4. 4
    Otropurified by silica gel column chromatography (1:3 v/v ethyl acetate/petroleum ether)

Procedimiento

Compound 25 (1.0 equiv.) was dissolved in DMF (40 mL) at room temperature. To this mixture bis(2-bromoethyl)amine (1.0 equiv.) was added, following the addition of NaOH (2.0 equiv.). After being stirred for 2 Hours at room temperature, the reaction mixture was poured into ice-cold water (200 mL) to get crude product. The crude solid was filtered and washed several times with water and purified by silica gel column chromatography (1:3 v/v ethyl acetate/petroleum ether) to provide a yellow solid (380.9 mg, 82% yield).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09402819B2uspto-grants-2016_08