3,4-Dinitrotoluene → N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamine

HRID 846019Notes

Reaction equation

HRID 846019 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-])=O.[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17]N.COCCOCCN(CCOCCOC)CCOCCOC>CS(C)=O>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:1][C:4]1[CH:5]=[C:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 118833,4-DinitrotolueneHCID 66053N,N-DimethylethylenediamineHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Product 1

HCID 18993729N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamineYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 3,4-dinitrotoluene (3.64 g, 20 mmol) and N,N-dimethylethylenediamine (1.76 g, 20 mmol) was heated at 80° C. in dimethyl sulfoxide and catalytic amount of TDA-1 for 2 hours. N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamine was isolated in 80% yield (3.6 g, 16 mmol) after aqueous work-up. Quaternization was achieved in quantitative yield with methyl iodide and dimethylformamide. Its melting point was 225°-7° C.

Sources & evidence

ORD record
ord-456301b9343f4a538becc55c45e476ae
Source dataset
uspto-grants-1992_08
Patent number
US05135543

Reaction notes

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