Toluene → N-allyl-N-methyl-3-[(3-methyl-4-nitrophenyl)amino]-N-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1-propanaminium p-toluene sulfonate

Reaction equation

[CH3:1][N:2]([CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[CH:22]=1)[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1.[C:31]1([CH3:44])[CH:36]=[CH:35][C:34]([S:37]([O:40]CC=C)(=[O:39])=[O:38])=[CH:33][CH:32]=1.[C:45]1(C)C=CC=C[CH:46]=1>>[C:31]1([CH3:44])[CH:32]=[CH:33][C:34]([S:37]([O-:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1.[CH2:1]([N+:2]([CH3:31])([CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=1)[CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([CH3:30])[CH:22]=1)[CH:45]=[CH2:46]

Participants

Reactant 3

HCID 1140Toluene

HCID 78587Allyl p-toluenesulphonate

HCID 86731947N1-Methyl-N3-(3-methyl-4-nitrophenyl)-N1-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1,3-propanediamine

Product 1

HCID 86731945N-allyl-N-methyl-3-[(3-methyl-4-nitrophenyl)amino]-N-{3-[(3-methyl-4-nitrophenyl)amino]propyl}-1-propanaminium p-toluene sulfonate

Procedure

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%).