Nitrobenzene → 1,4-Benzenediamine, N-(4-nitrophenyl)-

HRID 975602Notes

Reaction equation

HRID 975602 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:10]1([NH2:17])[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.[OH2:18].O.O.O.O.[OH-].C[N+:25]([CH3:28])(C)[CH3:26]>CS(C)=O>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:17])=[CH:11][CH:12]=2)=[CH:6][CH:5]=1)=[O:3].[N+:1]([C:4]1[CH:5]=[CH:6][C:26]([NH:25][C:28]2[CH:8]=[CH:9][C:4]([NH:16][C:13]3[CH:14]=[CH:15][C:10]([N:17]=[O:18])=[CH:11][CH:12]=3)=[CH:5][CH:6]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:17])=[CH:11][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 7416NitrobenzeneHCID 7814P-PhenylenediamineHCID 82620Tetramethylammonium Hydroxide Pentahydrate

Product 3

HCID 51013931,4-Benzenediamine, N-(4-nitrophenyl)-HCID 15219934N,N'-(4-nitrosophenyl)-1,4-phenylenediamineHCID 19959741N-(4-nitrophenyl)-N'-(4-nitrosophenyl)-1,4-phenylenediamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Nitrobenzene (2 ml, 0.02 mole) was added via a syringe to a stirring solution containing 1.08 g (0.01 mole) of 1,4-phenylenediamine, 3.6 g (0.02 mole) of tetramethylammonium hydroxide pentahydrate in 2 ml of dimethylsulfoxide under nitrogen at 70° C. The solution was stirred at such condition for 4 hours. An aliquot was taken out for LC, MS, LC-MS analyses. N,N'-(4-nitrosophenyl)-1,4-phenylenediamine, N-(4-nitrophenyl)-N'-(4-nitrosophenyl)-1,4-phenylenediamine and N,N'-(4-nitrophenyl)-1,4-phenylenediamine were obtained.

Sources & evidence

ORD record
ord-393baf6a614d48379d0c057df46969db
Source dataset
uspto-grants-1997_03
Patent number
US05608111

Reaction notes

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