Diglycolamine → 4-Chloro-2-(beta-hydroxyethoxyethyl)amino-6-(beta-hydroxyethoxyethyl)aminonitrobenzene

HRID 231377Notes

Reaction equation

HRID 231377 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].[NH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19]>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[C:4]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])[CH:7]=1

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 292282,4,6-Trichloronitrobenzene

Product 1

HCID 200710944-Chloro-2-(beta-hydroxyethoxyethyl)amino-6-(beta-hydroxyethoxyethyl)aminonitrobenzene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture consisting of 0.1 mole (22.6 g) of 2,4,6-trichloronitrobenzene, 0.6 mole (63 g) of 2-(β-aminoethoxy)ethanol and 20 ml of dioxan is heated to reflux of the dioxon. After 4 hours, the reaction mixture is poured onto to 200 g of ice. The product expected crystallizes on acidifying with concentrated hydrochloric acid. After draining, washing with water and drying by heating under vacuum, the product is recrystallized from acetonitrile and then from toluene. It melts at 83° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux of the dioxon
  3. customThe product expected crystallizes
  4. washwashing with water
  5. customdrying
  6. temperatureby heating under vacuum
  7. customthe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4e26d05449f846529a1c30fbcf8ff566
Source dataset
uspto-grants-1989_07
Patent number
US04845293

Reaction notes

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