Potassium Carbonate → [1,1'-Biphenyl]-4-amine, N,N-bis(3,4-dimethylphenyl)-

HRID 2397069노트

반응식

HRID 2397069 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:4][C:3]=1[CH3:17].I[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].CCCCCCCCCCCCC>[CH3:16][C:11]1[CH:10]=[C:9]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([CH3:17])[CH:4]=2)[C:28]2[CH:29]=[CH:30][C:25]([C:22]3[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=3)=[CH:26][CH:27]=2)[CH:14]=[CH:13][C:12]=1[CH3:15]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 153224-IodobiphenylHCID 614511Bis(3,4-dimethylphenyl)amine

생성물 1

HCID 10595766[1,1'-Biphenyl]-4-amine, N,N-bis(3,4-dimethylphenyl)-수율 71.2%

시약·촉매·용매 2

HCID 24463Copper sulfate pentahydrate촉매HCID 12388Tridecane용매

실험 절차

In a 500-ml three-neck flask were placed 31 g of 3,3',4,4'-tetramethyldiphenylamine synthesized in Example 3 (1), 40 g of 4-iodobiphenyl, 19 g of anhydrous potassium carbonate, 2 g of copper sulfate pentahydrate and 20 ml of n-tridecane, and after carrying out the reaction for 28 hours at 200° C. under a nitrogen gas stream, the reaction mixture was cooled to room temperature. The reaction mixture was subjected to a column purification (solvent: n-hexane/toluene =10/1) with activated alumina and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and ethanol to provide 37 g of N,N-bis(3,4-dimethylphenyl)biphenyl-4-amine. (Melting point 119° to 120.5° C., colorless crystals, IR spectrum shown in FIG. 4)

후처리

  1. customIn a 500-ml three-neck flask were placed
  2. customthe reaction for 28 hours at 200° C. under a nitrogen gas stream
  3. customThe reaction mixture was subjected to a column purification (solvent: n-hexane/toluene =10/1) with activated alumina
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of ethyl acetate and ethanol

출처 및 근거

ORD 기록
ord-5194ac011c98473fb848448b99186177
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05495049

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