p-Toluidine → N-(4-methylphenyl)-2,6-dinitroaniline

HRID 1456939Notes

Reaction equation

HRID 1456939 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:10]2[C:11]([N+:19]([O-:21])=[O:20])=[CH:12][CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 118141-Chloro-2,6-dinitrobenzene

Product 1

HCID 54444801N-(4-methylphenyl)-2,6-dinitroanilineYield 98.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.8 g (7.4 mmol) of p-toluidine and 1.5 g of 1-chloro-2,6-dinitrobenzene were dissolved in 15 ml of dimethyl sulfoxide and 1.5 g (14.8 mmol) of triethylamine was added thereto. After stirring at 80° to 90° C. for 12 hours, ethyl acetate was added and the reaction mixture was washed with water and dried over magnesium sulfate. After concentrating, the residue was purified by silica gel column chromatography. Thus 2.0 g of N-(4-methylphenyl)-2,6-dinitroaniline was obtained. This product was dissolved in a mixture of 20 ml of methanol with 40 ml of tetrahydrofuran and hydrogenated in the presence of palladium-carbon at room temperature under atmospheric pressure. After filtering off the catalyst, the solvent was distilled off under reduced pressure. Thus 1.6 g of the title compound was obtained.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationAfter concentrating
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cbb226a902704043b8540e94b525bb17
Source dataset
uspto-grants-1998_12
Patent number
US05846969

Reaction notes

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