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

HRID 505849

반응식

HRID 505849 반응식
[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

참가 물질

6

반응물 3

HCID 6115AnilineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

생성물 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine수율 85.1%

시약·촉매·용매 2

HCID 83681Tris(1,1-dimethylethyl)phosphine촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-436b11bfe6524980acbbc6d806a24022
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781579B2

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