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

HRID 249207

反応式

HRID 249207 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fae3e4d95f6415aba754cbf9b74f918
出典データセット
uspto-grants-1993_05
特許番号
US05213699

関連ノート

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