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

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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).

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