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

HRID 2104471노트

반응식

HRID 2104471 반응식
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

참가 물질

7

반응물 3

HCID 6115AnilineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

생성물 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine수율 88.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-촉매HCID 1140Toluene용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6521d068383e4feb8e2907b02859580e
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576484B2

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