2,4,6-Trinitrotoluene → N,N-Dimethyl-2-(2,4,6-trinitrophenyl)ethen-1-amine

HRID 1740509Notes

Reaction equation

HRID 1740509 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[C:5]=1[CH3:16])([O-:3])=[O:2].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[CH3:19][N:20]([CH:22]=[CH:16][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])[CH3:21]

Participants

3

Reactant 2

HCID 83762,4,6-TrinitrotolueneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54382168N,N-Dimethyl-2-(2,4,6-trinitrophenyl)ethen-1-amineYield 90%

Procedure

A mixture of 2,4,6-trinitrotoluene (0.5 g, 2.2 mmol) and N,N-dimethylformamide dimethyl acetal (2.7 ml) was refluxed for 2 h under nitrogen atmosphere. A dark purple red product was separated. N,N-dimethylformamide dimethyl acetal was removed under reduced pressure to give the title compound (0.56 g, 90% yield). m.p.: 155-157° C.; IR (KBr): 1635, 1585, 1530 cm-1; 1H NMR (CDCl3): δ 3.05 (s, 6H, 2×CH3); 5.65 (d, J=13.17 Hz, 1H, α-CH); 6.87 (d, J=13.2 Hz, 1H, β-CH); 8.55 (s, 2H, Ar--H); UV: Imax: 474 nm (CH3CN).

Workup

  1. temperaturewas refluxed for 2 h under nitrogen atmosphere
  2. customA dark purple red product was separated
  3. customN,N-dimethylformamide dimethyl acetal was removed under reduced pressure

Sources & evidence

ORD record
ord-6ca0b484243f4a6487413ba37cdd4c94
Source dataset
uspto-grants-1999_10
Patent number
US05969155

Reaction notes

Loading…