Reacción #155360

ord-36d795d1da95405ea6c75daa91c54980

Ecuación de reacción

Cc1cc(NCCCN(C)CCCNc2ccc([N+](=O)[O-])c(C)c2)ccc1[N+](=O)[O-]
N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine
C=CCOS(=O)(=O)c1ccc(C)cc1
allyl p-toluene sulfonate
Cc1ccccc1
toluene
C=CC[N+](C)(CCCNc1ccc([N+](=O)[O-])c(C)c1)CCCNc1ccc([N+](=O)[O-])c(C)c1.Cc1ccc(S(=O)(=O)[O-])cc1
product
C=CC[N+](C)(CCCNc1ccc([N+](=O)[O-])c(C)c1)CCCNc1ccc([N+](=O)[O-])c(C)c1.Cc1ccc(S(=O)(=O)[O-])cc1
N-allyl-N-methyl-3-[(3-methyl-4-nitrophenyl)amino]-N-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1-propanaminium p-toluene sulfonate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroseparated out in the form of an oily substance
  2. 2
    OtroThis oil was separated from the supernatant liquid
  3. 3
    Otroby decanting
  4. 4
    Otrodried
  5. 5
    TemperaturaOn further cooling the oil
  6. 6
    Otroafter drying could
  7. 7
    Otrobe crushed

Procedimiento

N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine (60.2 g, 0.14 mol) from step 7.1 was heated under reflux with allyl p-toluene sulfonate (34.0 g, 0.16 mol) in 500 ml toluene for 6 hours. As the reaction progressed the product separated out in the form of an oily substance. This oil was separated from the supernatant liquid by decanting and dried. On further cooling the oil initially solidified to a glassy material and after drying could be crushed to afford the product as a brown powder. Yield: 66.0 g (72.5%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08821592B1uspto-grants-2014_09