1-Iodonaphthalene → N,N-Bis(3,4-dimethylphenyl)naphthalen-1-amine

HRID 1081553ノート

反応式

HRID 1081553 の反応式
[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[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[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:27]2[C:28]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=[CH:25][CH:26]=2)[CH:14]=[CH:13][C:12]=1[CH3:15]

参加物

6

反応物 3

HCID 70041-IodonaphthaleneHCID 11430Potassium CarbonateHCID 614511Bis(3,4-dimethylphenyl)amine

生成物 1

HCID 23362688N,N-Bis(3,4-dimethylphenyl)naphthalen-1-amine収率 37.4%

試薬・触媒・溶媒 2

HCID 24463Copper sulfate pentahydrate触媒HCID 12388Tridecane溶媒

実験手順

In 100-ml three-neck flask were placed 7.2 g of 3,3',4,4'-tetramethyldiphenylamine synthesized in Example 3 (1), 12.2 g of 1-iodonaphthalene, 5 g of anhydrous potassium carbonate, 0.5 g of copper sulfate pentahydrate and 10 ml of n-tridecane, and after carrying out the reaction for 25 hours at 200° C. under a nitrogen gas atmosphere, the reaction mixture was cooled to room temperature. The reaction mixture was subjected to a column purification (solvent: n-hexane) with activated alumina and the solvent was distilled under reduced pressure. The residue was recrystallized from ethanol to provide 4.2 g of N,N-bis(3,4-dimethylphenyl)naphthalene-1-amine. (Melting point 125° to 127° C., light yellow crystals, IR spectrum shown in FIG. 5.)

後処理

  1. customIn 100-ml three-neck flask were placed
  2. customthe reaction for 25 hours at 200° C. under a nitrogen gas atmosphere
  3. customThe reaction mixture was subjected to a column purification (solvent: n-hexane) with activated alumina
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-0380f5945a714f52868da1c076832ffe
出典データセット
uspto-grants-1996_12
特許番号
US05587263

反応ノート

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