2,5-Dichloronitrobenzene → 4-Chloro-N-[(4-chlorophenyl)methyl]-2-nitroaniline

HRID 1493315Notes

Reaction equation

HRID 1493315 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 69772,5-DichloronitrobenzeneHCID 660364-Chlorobenzylamine

Product 1

HCID 149529774-Chloro-N-[(4-chlorophenyl)methyl]-2-nitroanilineYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g of 2,5-dichloronitrobenzene and 36.9 g of 4-chlorobenzylamine are heated for two hours at 135° C., it being necessary for the temperature always to be kept below 140° C. After cooling, the mixture is taken up with water and extracted with ethyl acetate. After drying over magnesium sulfate and evaporation under vacuum, the residue is taken up with ether and the crystals obtained are filtered off and washed with ether to give 22.3 g of 2-(4-chlorophenylmethylamino)-5-chloronitrobenzene in the form of crystals melting at 120° C.

Workup

  1. customto be kept below 140° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying over magnesium sulfate and evaporation under vacuum
  5. customthe crystals obtained
  6. filtrationare filtered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-a129c4343bb242aa91582b4afeb048b5
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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