Sulfuric Acid → 4-((2,4-Dinitrophenyl)diazenyl)-2,5-bis(2-ethylhexyloxy)aniline

HRID 1050494

Reaktionsgleichung

Reaktionsgleichung von HRID 1050494
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[N:14](OS(=O)(=O)O)=O.S(=O)(=O)(O)O.[CH2:26]([CH:28]([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:29][O:30][C:31]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])=[CH:34][C:32]=1[NH2:33])[CH3:27]>C(O)(=O)C.C(O)(=O)CC.S(=O)(=O)(O)N>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[N:6]=[N:14][C:36]1[C:35]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])=[CH:34][C:32]([NH2:33])=[C:31]([O:30][CH2:29][CH:28]([CH2:26][CH3:27])[CH2:47][CH2:48][CH2:49][CH3:50])[CH:37]=1)([O-:3])=[O:2]

Komponenten

8

Edukt 4

HCID 1118Sulfuric AcidHCID 73212,4-DinitroanilineHCID 82157Nitrosylsulfuric acidHCID 896017572,5-Bis(2-ethylhexyloxy)aniline

Produkt 1

HCID 896020744-((2,4-Dinitrophenyl)diazenyl)-2,5-bis(2-ethylhexyloxy)anilineAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 1032Propionic AcidLösungsmittelHCID 5987Sulfamic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
3 °C

Versuchsvorschrift

2,4-Dinitroaniline (3.7 g, 0.02 mol) is suspended in a mixture of acetic acid (20 ml) and propionic acid (10 ml) and cooled to 3° C. 40% (w/w) nitrosyl sulfuric acid in sulfuric acid (6.4 g, 0.02 mol) is added dropwise and stirring continued for 30 minutes to give a pale yellow solution. Crude 2,5-bis(2-ethylhexyloxy)aniline (0.02 mol) solution is diluted with IMS (200 ml) and 10% sulfamic acid solution (20 ml) added, followed by ice (200 g). The above pale yellow diazonium salt solution is slowly added with stirring and a dark oil rapidly separated. The mixture is stirred overnight and the water is decanted off. The crude product (8.3 g) is dissolved in 25/75 dichloromethane/hexane and purified over silica gel, the required product eluting with 50/50 hexane/dichloromethane. Evaporation and trituration with methanol gave 4-((2,4-dinitrophenyl)diazenyl)-2,5-bis(2-ethylhexyloxy)-aniline as a violet-blue crystalline solid (4.2 g, 39%).

Aufarbeitung

  1. customto give a pale yellow solution
  2. additionadded
  3. stirringwith stirring
  4. customa dark oil rapidly separated
  5. stirringThe mixture is stirred overnight
  6. customthe water is decanted off
  7. dissolutionThe crude product (8.3 g) is dissolved in 25/75 dichloromethane/hexane
  8. custompurified over silica gel
  9. washthe required product eluting with 50/50 hexane/dichloromethane
  10. customEvaporation and trituration with methanol

Quellen und Nachweise

ORD-Eintrag
ord-ad3dc1c3e5ec46369746086868cd0366
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09383621B2

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