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

HRID 1050494

反応式

HRID 1050494 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1032Propionic Acid溶媒HCID 5987Sulfamic Acid溶媒

反応条件

温度
3 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ad3dc1c3e5ec46369746086868cd0366
出典データセット
uspto-grants-2016_07
特許番号
US09383621B2

関連ノート

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