N,N'-Diphenyl-P-Phenylenediamine → N,N'-Bis(4-chlorophenyl)-N,N'-diphenyl-1,4-phenylenediamine

HRID 2325

반응식

HRID 2325 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.I[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].[Cl:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1Cl>CCCCCC.[Cu].C(Cl)Cl>[C:15]1([N:14]([C:57]2[CH:58]=[CH:59][C:54]([Cl:53])=[CH:55][CH:56]=2)[C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:9][CH:10]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

9

반응물 5

HCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 72391,2-DichlorobenzeneHCID 11430Potassium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 2855718-Crown-6

생성물 1

HCID 21851001N,N'-Bis(4-chlorophenyl)-N,N'-diphenyl-1,4-phenylenediamine

시약·촉매·용매 3

HCID 23978Copper촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매

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온도
200 °C

실험 절차

A 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser, was charged with N,N'-diphenyl-1,4-phenylenediamine (13.0 g, 0.05 mol), 4-iodochlorobenzene (31.0 g, 0.13 mol), copper bronze powder (12.7 g, 0.20 mol), 18-crown-6 ether (2.6 g, 0.10 mol), powdered potassium carbonate (50.1 g. 0.36 mol) and 1,2-dichlorobenzene (120 mL). With a slow purge of nitrogen through the condenser, the reaction vessel was placed in an oil bath and the stirred reaction was heated at 200° C. for 20 hours. The hot reaction mixture was filtered through a bed of filtering aid, which was washed with toluene (50 mL), and the filtrate was concentrated on a rotavapor under reduced pressure. The solvent residue was further removed with a Kugelrohr apparatus to afford a dark brown viscous oil. Flash chromatography on a silica gel column (5×25 cm, 5% CH2Cl2 in hexane as eluent) afforded 9.6 g of grey-white solid. The crude product was further washed with toluene and acetone to provide 6.1 g (25%) of off-white powdered material. The polymer of this example is useful for hole transport materials in light-emitting diode devices.

후처리

  1. customA 1 L, three-necked, round-bottomed flask, equipped with an overhead stirrer, a nitrogen inlet and a reflux condenser
  2. customWith a slow purge of nitrogen through the condenser
  3. customthe reaction vessel was placed in an oil bath
  4. customthe stirred reaction
  5. filtrationThe hot reaction mixture was filtered through a bed
  6. filtrationof filtering aid, which
  7. washwas washed with toluene (50 mL)
  8. concentrationthe filtrate was concentrated on a rotavapor under reduced pressure
  9. customThe solvent residue was further removed with a Kugelrohr apparatus
  10. customto afford a dark brown viscous oil

출처 및 근거

ORD 기록
ord-76651472f2d84918bce8909e6a061689
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728801

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