Toluene → N,N'-dianisyl-1,4-phenylenediamine

HRID 50462

반응식

HRID 50462 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1([NH2:17])[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.C[C:19](C)([O-:21])C.[Na+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:31]CCCCC>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:31]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([NH:17][CH2:30][C:24]2[CH:29]=[CH:28][C:27]([O:21][CH3:19])=[CH:26][CH:25]=2)=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 1140TolueneHCID 77304-BromoanisoleHCID 7814P-PhenylenediamineHCID 8058HexaneHCID 23676156Sodium t-butoxide

생성물 1

HCID 21301606N,N'-dianisyl-1,4-phenylenediamine수율 72%

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
90 °C

실험 절차

A flame-dried one liter three neck round bottom flask was charged with 4-bromoanisole (50.4 g, 0.26 mole), 1,4-phenylenediamine (12.0 g, 0.11 mole), 1,1 ′-bis(diphenylphosphino)ferrocene (1.776 g, 0.0032 mole), tris(dibenzylideneacetone)dipalladium(0) (0.98 g, 0.001 mole), sodium tert-butoxide (31.2 g, 0.32 mole), and anhydrous toluene (350 ml). The reaction mixture was heated to 90° C. for 48 hours. The reaction mixture was cooled to room temperature and hexane (400 ml) was added. The solid was filtered and dissolved in ethanol (400 ml). Sodium dithionite (20.0 g) was dissolved in 300 ml water and added to the ethanol solution. This was heated to reflux for 30 minutes. After the solution was cooled to room temperature, the solid was filtered off and washed with water to give 25.7 g (72%) of N,N′-dianisyl-1,4-phenylenediamine.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in ethanol (400 ml)
  4. dissolutionSodium dithionite (20.0 g) was dissolved in 300 ml water
  5. additionadded to the ethanol solution
  6. temperatureThis was heated
  7. temperatureto reflux for 30 minutes
  8. temperatureAfter the solution was cooled to room temperature
  9. filtrationthe solid was filtered off
  10. washwashed with water

출처 및 근거

ORD 기록
ord-361d3f1358d749a78e0447ed25911790
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710906B2

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