Potassium Iodide → N,N'-Dibenzyl-N,N'-diphenyl-p-phenylenediamine

HRID 249207

반응식

HRID 249207 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.[OH-].[K+].[I-].[K+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:25]([N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]1[CH:12]=[CH:13][C:8]([N:7]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 6319N,N'-Diphenyl-P-PhenylenediamineHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

생성물 1

HCID 15701549N,N'-Dibenzyl-N,N'-diphenyl-p-phenylenediamine

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

A solution of N,N'-diphenyl-p-phenylenediamine (26 g, 0.1 mol) in toluene (400 ml) is treated sequentially with powdered potassium hydroxide (19.3 g, 0.3 mol), potassium iodide (1.7 g, 0.01 mol) and tetrabutylammonium bromide (1.6 g, 0.005 mol). The resulting mixture is vigorously stirred while benzyl chloride (27.9 g, 0.22 mol) is added dropwise. The mixture is slowly warmed to 90° C. over a one-hour period and then held there for four hours. The mixture is allowed to cool and methylene chloride (100 ml) is added. The resulting mixture is filtered and concentrated to a solid that is washed with water and dried. The title compound is obtained in a yield of 24.8 g (56%) as a tan solid melting at 145°-150° C.

후처리

  1. additionis added dropwise
  2. temperatureto cool
  3. filtrationThe resulting mixture is filtered
  4. concentrationconcentrated to a solid
  5. washthat is washed with water
  6. customdried

출처 및 근거

ORD 기록
ord-4fae3e4d95f6415aba754cbf9b74f918
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05213699

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