1,5-Dichloroanthraquinone → 1,5-Bis(4-cyclohexylphenylamino)-anthraquinone

HRID 256276

反応式

HRID 256276 の反応式
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:19]1([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C:32]([O-])(=O)[CH3:33].[Na+].[N+:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([O-])=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO>[CH:19]1([C:25]2[CH:26]=[CH:27][C:28]([NH:29][C:2]3[C:15]4[C:14](=[O:16])[C:13]5[C:8](=[C:9]([NH:37][C:40]6[CH:45]=[CH:44][C:43]([CH:32]7[CH2:33][CH2:4][CH2:3][CH2:2][CH2:15]7)=[CH:42][CH:41]=6)[CH:10]=[CH:11][CH:12]=5)[C:7](=[O:18])[C:6]=4[CH:5]=[CH:4][CH:3]=3)=[CH:30][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

参加物

7

反応物 4

HCID 67111,5-DichloroanthraquinoneHCID 7416NitrobenzeneHCID 807644-CyclohexylbenzenamineHCID 517045Sodium Acetate

生成物 1

HCID 201633301,5-Bis(4-cyclohexylphenylamino)-anthraquinone

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 887Methanol溶媒

実験手順

In a round bottom flask equipped with stirrer, thermometer, and nitrogen inlet is added 2.77 g (0.1M) 1,5-bischloroanthraquinone and 3.5 g (0.2M) of 4-cyclohexylaniline. 3.0 g anhydrous sodium acetate and 0.1 g anhydrous copper acetate are added as acid acceptor and reaction catalyst respectively. 50 g nitrobenzene are added and the stirred mass is heated to reflux under nitrogen atmosphere. The reaction is allowed to proceed for two hours at 185° C. Upon cooling, 50 g methanol is added and the crude dye separated by vacuum filtration. Subsequent purification by recrystalization and chromatography from alumina using toluene as the elvent affords the magneta pleochroic dye 1,5-bis(4-cyclohexylphenylamino)-anthraquinone. The optical order parameter was measured as 0.7.

後処理

  1. customIn a round bottom flask equipped with stirrer
  2. customacceptor and reaction catalyst respectively
  3. temperaturethe stirred mass is heated
  4. temperatureto reflux under nitrogen atmosphere
  5. temperatureUpon cooling
  6. customthe crude dye separated by vacuum filtration
  7. customSubsequent purification
  8. customby recrystalization and chromatography from alumina

出典と根拠

ORDレコード
ord-8d56c5b5a35a4fcda4c347d4ddb3d7c7
出典データセット
uspto-grants-1987_10
特許番号
US04702561

関連ノート

読み込み中…