Aniline → N,N,N'-triphenyl-4-phenylenediamine

HRID 2193979

反応式

HRID 2193979 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:4]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

参加物

6

反応物 3

HCID 6115AnilineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

生成物 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine収率 85.1%

試薬・触媒・溶媒 2

HCID 83681Tris(1,1-dimethylethyl)phosphine触媒HCID 1140Toluene溶媒

実験手順

4-bromo triphenylamine 7.6 g (23.45 mmol), aniline 21.85 g (0.235 mol), sodium tert-butoxide 6.76 g (70 mmol). Pd2(dba)3[(tris(dibenzilidene acetone)dipalladium(0))]0.86 g (0.938 mmol) and tri(tert-butyl)phosphine 0.23 g (1.173 mmol) in 500 ml round bottom flask were dissolved with toluene 200 ml, and refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature, and 200 ml of distilled water was added thereto to extract an organic layer. The organic layer was dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give N,N,N′-triphenyl-p-phenylenediamine (6.71 g, 85%).

後処理

  1. temperaturerefluxed for 12 hours
  2. customAfter the reaction was terminated
  3. addition200 ml of distilled water was added
  4. extractionto extract an organic layer
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography
  8. concentrationThe eluate was concentrated
  9. customdried

出典と根拠

ORDレコード
ord-b54f5ef4c5234d9eb75bd3d9bc0f45d7
出典データセット
uspto-grants-2012_12
特許番号
US08329953B2

関連ノート

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