2,4,6-Trichloronitrobenzene → 4-Chloro-2-(beta-diethylaminoethyl)amino-6-(beta-diethylaminoethyl)aminonitrobenzene

HRID 981822Notes

Reaction equation

HRID 981822 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14]>O>[Cl:8][C:6]1[CH:5]=[C:4]([NH:18][CH2:17][CH2:16][N:15]([CH2:19][CH3:20])[CH2:13][CH3:14])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:18][CH2:17][CH2:16][N:15]([CH2:19][CH3:20])[CH2:13][CH3:14])[CH:7]=1

Participants

4

Reactant 2

HCID 292282,4,6-TrichloronitrobenzeneHCID 60993N,N-Diethylethylenediamine

Product 1

HCID 200710864-Chloro-2-(beta-diethylaminoethyl)amino-6-(beta-diethylaminoethyl)aminonitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

0.2 mole (45.3 g) of 2,4,6-trichloronitrobenzene is added portionwise, with stirring, to 180 ml of N,N-diethylethylenediamine, heated to 60° C. After the end of the addition, heating is continued for 30 minutes. The reaction mixture is diluted with 180 ml of iced water. The expected product precipitates. It is filtered off, washed with water and then dried under vacuum at 60° C. in the presence of phosphorus pentoxide. After recrystallization from 96° ethanol, it melts at 90° C.

Workup

  1. additionAfter the end of the addition
  2. temperatureheating
  3. customThe expected product precipitates
  4. filtrationIt is filtered off
  5. washwashed with water
  6. dry with materialdried under vacuum at 60° C. in the presence of phosphorus pentoxide
  7. customAfter recrystallization from 96° ethanol, it melts at 90° C.

Sources & evidence

ORD record
ord-375efb024509435290011ff3391e9493
Source dataset
uspto-grants-1991_02
Patent number
US04992586

Reaction notes

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