Reaction #155359

Reaction equation

5-fluoro-2-nitrotoluene

sodium carbonate

3,3′-Diamino-N-methyldipropylamine

→

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

Solvents

toluene

Conditions

Workup

1. 1
   Other(exothermic reaction)
2. 2
   Otherto precipitate
3. 3
   Filtrationwhich were filtered off
4. 4
   ConcentrationThe organic phase was then concentrated down under vacuum in a rotovap
5. 5
   Otherto afford the product as a residue in the form of a yellow orange oil

Procedure

To 5-fluoro-2-nitrotoluene (50.0 g, 0.32 mol) was added sodium carbonate (17.1 g, 0.16 mol) at 60° C. 3,3′-Diamino-N-methyldipropylamine (23.7 g, 0.16 mol) was then carefully added dropwise (exothermic reaction). The resulting mixture was heated at 100° C. for 12 hours. 100 ml toluene were added to the cooled reaction mixture causing the inorganic salts to precipitate, which were filtered off. The organic phase was then concentrated down under vacuum in a rotovap to afford the product as a residue in the form of a yellow orange oil. Yield: 52.5 g (78.4%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=1.71 (m, 4H); 2.18 (s, 3H); 2.40 (m, 4H); 2.55 (s, 6H); 3.17 (m, 4H); 6.45 (s, 2H); 6.48 (d, 2H); 7.08 (br., 2×NH); 7.92 (d, 2H).

Source