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

HRID 2104471

反応式

HRID 2104471 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:9]1([N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[CH:6]=[CH:7][C:2]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 3

HCID 6115AnilineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

生成物 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine収率 88.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒HCID 1140Toluene溶媒2 回

実験手順

In a two-neck round bottom flask, (4-bromo-phenyl)-diphenyl-amine (12 g, 0.037 mol), aniline (16.26 ml, 0.178 mol), BINAP (0.4 g, 3% mol), Pd(OAc)2 (7.4 g, 4% mol), and NaOtBu (17.2 g, 0.178 mol) are dissolved in toluene (300 mL), and then are maintained for 18 hours by reflux. On completion of the reaction, the flask having the resultant solution is cooled, and then toluene, a solvent of the reaction, is removed from the resultant solution. After that, the resultant solution having no toluene reacts on methylene-chloride and water, and then methylene-chloride is removed therefrom, and is performed by silica gel column chromatography with a solvent of methylene-chloride and hexane at a ratio of 2 to 1. After that, the solvent is removed from the resultant solution of completing silica gel column chromatography, and is recrystallized and filtered with methylene-chloride and petroleum ether, thereby obtaining a white solid, N,N,N′-triphenyl-benzene-1,4-diamine (11.0 g, 88%).

後処理

  1. temperatureare maintained for 18 hours
  2. temperatureby reflux
  3. customOn completion of the reaction
  4. temperatureis cooled
  5. customis removed from the resultant solution
  6. customreacts on methylene-chloride and water
  7. custommethylene-chloride is removed
  8. customAfter that, the solvent is removed from the resultant solution of completing silica gel column chromatography
  9. customis recrystallized
  10. filtrationfiltered with methylene-chloride and petroleum ether

出典と根拠

ORDレコード
ord-6521d068383e4feb8e2907b02859580e
出典データセット
uspto-grants-2009_08
特許番号
US07576484B2

関連ノート

読み込み中…