Dodecane → N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidine

HRID 1762411

反応式

HRID 1762411 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([CH3:15])[CH:9]=2)[CH:5]=[CH:4][C:3]=1[NH2:16].[OH-].[K+].CCCCC[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].I[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1>[Cu](I)I.O>[CH3:38][C:35]1[CH:36]=[CH:37][C:32]([N:16]([C:28]2[CH:27]=[CH:26][C:25]([CH3:24])=[CH:30][CH:29]=2)[C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH:13]=[CH:12][C:11]([N:14]([C:13]4[CH:8]=[CH:9][C:10]([CH3:15])=[CH:11][CH:12]=4)[C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[C:10]([CH3:15])[CH:9]=3)=[CH:7][C:2]=2[CH3:1])=[CH:33][CH:34]=1

参加物

7

反応物 4

HCID 8182DodecaneHCID 8413o-TolidineHCID 122074-Iodotoluene2 回HCID 14797Potassium Hydroxide2 回

生成物 1

HCID 4396362N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidine収率 75.7%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒2 回HCID 962Water溶媒2 回

反応条件

温度
180 °C

実験手順

In a round flask were charged 3.14 g (13.8 mmol) of o-tolidine, 40 g of potassium hydroxide, 400 mg of copper iodide, and 30 ml of n-dodecane, and the mixture was heated at 180° C. in a nitrogen stream. To the mixture was added dropwise 24.0 g (110 mmol) of 4-iodotoluene, and the heating at 180° C. was continued for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with toluene. In order to assure completion of the reaction, the solvent was once removed by distillation, and 40 g of potassium hydroxide, 400 mg of copper iodide, and 24.0 g (110 mmol) of 4-iodotoluene were added to the residue, followed by allowing to react at 180° C. for 5 hours in a nitrogen stream. Water was added, and the mixture was extracted with toluene. The extract was dried over sodium sulfate and then treated with activated clay. The solvent was removed by distillation to obtain 5.98 g (yield: 75.7%) of N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidine, which was recrystallized from a mixed solvent of toluene/acetone/hexane to obtain 4.32 g (final yield: 54.7%) of a white crystal having a melting point of 174°-175° C. Analysis by high performance liquid chromatography revealed that the product has a high purity of 99.9%.

後処理

  1. extractionthe mixture was extracted with toluene
  2. customcompletion of the reaction
  3. additionwere added to the residue
  4. customto react at 180° C. for 5 hours in a nitrogen stream
  5. extractionthe mixture was extracted with toluene
  6. dry with materialThe extract was dried over sodium sulfate
  7. additiontreated with activated clay
  8. customThe solvent was removed by distillation

出典と根拠

ORDレコード
ord-32125315b1124f0a908f5956e55d5f64
出典データセット
uspto-grants-1989_05
特許番号
US04833054

関連ノート

読み込み中…