Iodine → 1,4-Benzenediamine, N1,N1,N4,N4-tetraphenyl-

HRID 6575

반응식

HRID 6575 반응식
[CH:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+].II>[Cu].[N+](C1C=CC=CC=1)([O-])=O>[C:15]1([N:14]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)=[CH:9][CH:10]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 807IodineHCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 11430Potassium CarbonateHCID 11575Iodobenzene

생성물 1

HCID 842071,4-Benzenediamine, N1,N1,N4,N4-tetraphenyl-수율 111.3%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7416Nitrobenzene용매

실험 절차

41.4 g of N,N′-diphenyl-p-phenylenediamine, 66 g of iodobenzene, 100 ml of nitrobenzene, 45 g of K2CO3, 10.8 g of copper powder, and I2 (trace) were put in a four-neck flask of 300-milliliter volume, and were refluxed gently over 24 hours by stirring the same while removing generated water by reflux. Subsequently, steam distillation was carried out, and when a distillate no longer came out, residues were filtered out after cooling, washed with water, and extracted using toluene. After removing toluene by distillation, ethanol was added to the residues, and the mixture was filtered. Recrystallization was carried out using a solvent of toluene and ethanol (toluene:ethanol=4:1 (by volume)), whereby 36.5 g of N,N,N′,N′-tetraphenyl-p-phenylenediamine was obtained. It had a melting point of 200° C. to 202° C.

후처리

  1. temperaturewere refluxed gently over 24 hours
  2. customwhile removing
  3. temperatureby reflux
  4. distillationSubsequently, steam distillation
  5. filtrationresidues were filtered out
  6. temperatureafter cooling
  7. washwashed with water
  8. extractionextracted
  9. customAfter removing toluene
  10. distillationby distillation, ethanol
  11. additionwas added to the residues
  12. filtrationthe mixture was filtered
  13. customRecrystallization

출처 및 근거

ORD 기록
ord-77814c110edc4862859dc162723022c7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083863B2

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