2-Chloroethanol → 2,2'-[(2-Chloro-5-nitro-1,4-phenylene)diazanediyl]di(ethan-1-ol)

HRID 1282963Notes

Reaction equation

HRID 1282963 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([NH2:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14].[CH2:16](Cl)[CH2:17][OH:18].[OH-].[Na+]>O>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([NH:12][CH2:16][CH2:17][OH:18])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 22034693HCID 22034693, compound

Product 1

HCID 224130822,2'-[(2-Chloro-5-nitro-1,4-phenylene)diazanediyl]di(ethan-1-ol)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

79.0 g (0.33 mole) of 1-beta-hydroxyethylamino-2-nitro-4-amino-5-chlorobenzene were dissolved in 150 ml methylglycol and 36 g (0.5 mole) ethylenechlorohydrin. 19.8 g of NaOH dissolved in 180 ml water were then added while stirring over a period of 3 hours at a bath temperature of 130°C. The final product was removed by suction after cooling and was recrystallized from water. Yield: 35 g 1,4-di-(beta-hydroxyethylamino)-2-nitro-5-chlorobenzene; m.p.: 127°-128°C. Analysis: C10H14N3O4Cl

Workup

  1. additionwere then added
  2. customThe final product was removed by suction
  3. temperatureafter cooling
  4. customwas recrystallized from water

Sources & evidence

ORD record
ord-218b4fd6cd4541ab9fb94879c1c432a3
Source dataset
uspto-grants-1976_08
Patent number
US03973900

Reaction notes

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