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

HRID 716594

反応式

HRID 716594 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bde5c400d61847b99d80e824321ef023
出典データセット
uspto-grants-2015_11
特許番号
US09190623B2

関連ノート

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