N,N'-Diphenyl-P-Phenylenediamine → N1,N1,N4-triphenyl-N4-(4-(phenylamino)phenyl)benzene-1,4-diamine

HRID 716594

반응식

HRID 716594 반응식
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:22]1[CH:40]=[CH:39][C:25]([N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]1([N:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:39]=[CH:40][C:22]([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[CH:9]=[CH:10][C:11]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:12][CH:13]=3)=[CH:23][CH:24]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

7

반응물 3

HCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

생성물 1

HCID 86718963N1,N1,N4-triphenyl-N4-(4-(phenylamino)phenyl)benzene-1,4-diamine수율 55.6%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

To a stirred solution of N1,N4-diphenylbenzene-1,4-diamine (6.5 g, 20.0 mmol) in toluene (400 mL), 4-bromo-N,N-diphenylaniline (7.9 g, 30.1 mmol) was added and the solution was degassed with nitrogen for 15 minutes. Palladium (II) acetate (45 mg, 0.2 mmol), triphenylphosphine (210 mg, 0.8 mmol) and sodium tert-butoxide (2.9 g, 30.1 mmol) were added and degassed with nitrogen for another 15 minutes. The reaction was refluxed overnight. The reaction mixture was filtered through Celite®, washed with toluene and the filtrate was concentrated under vacuum. It was then column chromatographed with hexane to 50% toluene/hexane to obtain 5.6 g (48%) of the desired product as a white solid.

후처리

  1. customthe solution was degassed with nitrogen for 15 minutes
  2. customdegassed with nitrogen for another 15 minutes
  3. temperatureThe reaction was refluxed overnight
  4. filtrationThe reaction mixture was filtered through Celite®
  5. washwashed with toluene
  6. concentrationthe filtrate was concentrated under vacuum
  7. customcolumn chromatographed with hexane to 50% toluene/hexane

출처 및 근거

ORD 기록
ord-bde5c400d61847b99d80e824321ef023
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09190623B2

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