2-Chloroethanol → 2-((4-Amino-2-chloro-5-nitrophenyl)amino)ethanol

HRID 1282962

Reaktionsgleichung

Reaktionsgleichung von HRID 1282962
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13](Cl)[CH2:14][OH:15].[OH-].[Na+]>O>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][CH2:13][CH2:14][OH:15])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 54842901,4-Benzenediamine, 2-chloro-5-nitro-

Produkt 1

HCID 54902712-((4-Amino-2-chloro-5-nitrophenyl)amino)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

18.7 g (0.1 mole) of 1,4-diamino-2-nitro-5-chlorobenzene were dissolved in 20 ml methylglycol and 12 g ethylenechlorohydrin (1.5 mole) and the solution then heated on a bath having a temperature of 120°C. 6.6 g of sodium hydroxide dissolved in 60 ml water were then slowly added dropwise over a period of 3 hours. Heating was then continued for 1 hour whereupon a chromatographic check wss made to ascertain whether most or all of the starting compound had been reacted. After cooling the mass was diluted with water and the precipitated hydroxyethylated compound was removed by suction. Recrystallation was effected from water and thereafter from a 20% acetic acid. Yield: 4.5 g; m.p.: 130°-131°C. Analysis: C8H10ClO3N3

Aufarbeitung

  1. customa temperature of 120°C
  2. additionwere then slowly added dropwise over a period of 3 hours
  3. temperatureHeating
  4. customhad been reacted
  5. temperatureAfter cooling the mass
  6. customthe precipitated hydroxyethylated compound was removed by suction

Quellen und Nachweise

ORD-Eintrag
ord-7dbc80d2dfcb4972b48b3f9643edad35
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03973900

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