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O-Xylene → N4,N4'-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4'-diamine

HRID 889801
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HRID 889801 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH2:9].[C:10](O[Na])([CH3:13])([CH3:12])[CH3:11].[C:16]1(C)[C:17]([CH3:22])=[CH:18][CH:19]=[CH:20][CH:21]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:20]1[CH:21]=[CH:16][C:17]([CH3:22])=[CH:18][CH:19]=1)[C:6]1[CH:8]=[CH:12][C:10]([C:13]2[CH:5]=[CH:4][C:3]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])=[CH:2][CH:1]=2)=[CH:11][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7237O-XyleneHCID 72502,4-DimethylanilineHCID 178418730sodium 2-methylpropan-2-olate

생성물 1

HCID 86597908N4,N4'-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4'-diamine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
촉매

실험 절차

Into a 1 liter three-necked reaction vessel fitted with a cooling tube and a mechanical stirrer, 88.5 g (0.2 mol) of (4′-(bromobiphenyl-4-yl)-(2,4-dimethylphenyl)-p-tolylamine, 26.7 g (0.22 mol) of 2,4-dimethylphenylamine, 2.2 g (0.01 mol) of palladium acetate, 11.1 g (0.02 mol) of bis(diphenylphosphino)ferrocene, 26.8 g (0.28 mol) of tert-butoxysodium and 400 mL of xylene were introduced to effect reflux for 5 hours in a nitrogen gas atmosphere and with heating in an oil bath. After the reaction was completed, the reaction mixture was left to cool to room temperature, followed by extraction with toluene/water, then washing with hydrochloric acid water, and thereafter distillation of the organic layer under reduced pressure and purification with a silica gel column (developer solvent: hexane/toluene=1:1) to give the desired N4,N4′-bis(2,4-dimethylphenyl)-N4-p-tolylbiphenyl-4,4′-diamine. The compound obtained was in a yield of 71.4 g corresponding to 74%. The compound obtained was measured with the same elementary analyzer as the above.

후처리

  1. customInto a 1 liter three-necked reaction vessel fitted with a cooling tube and a mechanical stirrer
  2. temperaturereflux for 5 hours in a nitrogen gas atmosphere
  3. temperaturewith heating in an oil bath
  4. waitthe reaction mixture was left
  5. extractionfollowed by extraction with toluene/water
  6. washwashing with hydrochloric acid water
  7. distillationdistillation of the organic layer
  8. customunder reduced pressure and purification with a silica gel column (developer solvent: hexane/toluene=1:1)

출처 및 근거

ORD 기록
ord-fbadf1c06a9b4113b9ce209a339d8ab0
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06994941B2

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