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

HRID 1050494

반응식

HRID 1050494 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 1032Propionic Acid용매HCID 5987Sulfamic Acid용매

반응 조건

온도
3 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ad3dc1c3e5ec46369746086868cd0366
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09383621B2

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