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

HRID 893345Notes

Reaction equation

HRID 893345 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-5ab13f76a8a94b68abb4500fd2be9b32
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

Loading…