1-Chloro-4-nitrobenzene → N-[(4-methoxy) phenyl]-N'[4-nitro phenyl] ethylene diamine

HRID 596241Notes

Reaction equation

HRID 596241 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[CH:7][CH:6]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>O>[CH3:10][O:9][C:8]1[CH:11]=[CH:12][C:5]([NH:4][CH2:3][CH2:2][NH:1][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 12666396N~1~-(4-Methoxyphenyl)ethane-1,2-diamine

Product 1

HCID 54530294N-[(4-methoxy) phenyl]-N'[4-nitro phenyl] ethylene diamineYield 278.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 0.1 mole (223 g) of N- β-aminoethyl paraanisidine and 0.447 mole (70.6 g) of parachloronitrobenzene is heated for 5 hours at 120°. After cooling the reaction mixture is poured into a liter of water and drying yields a crude product. This product after recrystallization in chlorobenzene, produces 80 g of N- [(4-methoxy) phenyl] - N'[4-nitro phenyl] ethylene diamine, which melts at 150°.

Workup

  1. temperatureis heated for 5 hours at 120°
  2. temperatureAfter cooling the reaction mixture
  3. customdrying
  4. customyields a crude product
  5. customThis product after recrystallization in chlorobenzene

Sources & evidence

ORD record
ord-3a4546306dcd4611bc98e28f18fcb7b3
Source dataset
uspto-grants-1977_03
Patent number
US04010200

Reaction notes

Loading…