Reacción #4335

ord-4c54e3751d4842d7a5094d5ea6aa2e59

Ecuación de reacción

NCCNc1cc(Cl)c(Cl)cc1[N+](=O)[O-]
4,5-dichloro-2-nitro-N-β-aminoethylaniline
NCCO
monoethanolamine
NCCNc1cc(NCCO)c(Cl)cc1[N+](=O)[O-]
2-chloro-5-β-aminoethylamino-4-nitro-N-(β-hydroxyethyl)aniline

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAn impurity is precipitated
  2. 2
    workup.ADDITIONby adding hydrochloric acid
  3. 3
    Otrois removed by filtration
  4. 4
    OtroThe expected product precipitates
  5. 5
    FiltraciónAfter filtration
  6. 6
    Otrodrying
  7. 7
    Otroit is purified as its hydrochloride
  8. 8
    Otrobefore being recrystallized from alcohol

Procedimiento

0.04 mole (10 g) of 4,5-dichloro-2-nitro-N-β-aminoethylaniline prepared in the 1st stage is heated in 40 ml of monoethanolamine for 30 minutes to 100° C. The reaction mixture is diluted with 450 ml of iced water. An impurity is precipitated by adding hydrochloric acid and is removed by filtration. The filtrate is made alkaline with concentrated sodium hydroxide solution. The expected product precipitates. After filtration and drying, it is purified as its hydrochloride before being recrystallized from alcohol. It melts at 160° C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725283uspto-grants-1988_02