Réaction #155360

ord-36d795d1da95405ea6c75daa91c54980

Équation de réaction

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

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreseparated out in the form of an oily substance
  2. 2
    AutreThis oil was separated from the supernatant liquid
  3. 3
    Autreby decanting
  4. 4
    Autredried
  5. 5
    TempératureOn further cooling the oil
  6. 6
    Autreafter drying could
  7. 7
    Autrebe crushed

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08821592B1uspto-grants-2014_09