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

HRID 231383Notes

Reaction equation

HRID 231383 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]>>[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

3

Reactant 2

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

Product 1

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

Conditions

Temperature
60 °C

Procedure

0.2 mole (45.3 g) of 2,4,6-trichloronitrobenzene is added in small portions to 180 ml of N,N-diethylethylenediamine heated to 60° C., with stirring. Heating is continued for 30 minutes after the addition is complete. The reaction medium is diluted with 180 ml of ice-cold water. The product expected precipitates. It is drained, washed with water and then dried under vacuum at 60° C. in the presence of phosphorous pentoxide. After recrystallizing from 96° ethanol, it melts at 90° C.

Workup

  1. temperatureHeating
  2. additionafter the addition
  3. customThe product expected precipitates
  4. washwashed with water
  5. dry with materialdried under vacuum at 60° C. in the presence of phosphorous pentoxide
  6. customAfter recrystallizing from 96° ethanol, it melts at 90° C.

Sources & evidence

ORD record
ord-b9395a4a1d4b451fbdaa41045f546ada
Source dataset
uspto-grants-1989_07
Patent number
US04845293

Reaction notes

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