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Dodecane → N,N'-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4'-yl]-N,N'-diphenyl-4,4''-diamino-p-terphenyl

HRID 1158221
ノート
印刷プレビュー

反応式

HRID 1158221 の反応式
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][C:4]([N:7]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.I[C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55]([C:58]3[CH:63]=[CH:62][C:61](I)=[CH:60][CH:59]=3)=[CH:54][CH:53]=2)=[CH:48][CH:47]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82]>C1(C)C=CC=CC=1.[Cu].C(OCC)(=O)C>[C:30]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:32][C:27]([N:7]([C:4]2[CH:3]=[CH:2][C:1]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:6][CH:5]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:46]4[CH:51]=[CH:50][C:49]([C:52]5[CH:57]=[CH:56][C:55]([C:58]6[CH:63]=[CH:62][C:61]([N:20]([C:80]7[CH:81]=[CH:82][C:77]([C:76]8[CH:71]=[CH:72][C:73]([N:7]([C:8]9[CH:9]=[CH:10][C:11]([C:14]%10[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=%10)=[CH:12][CH:13]=9)[C:4]9[CH:5]=[CH:6][C:1]([C:39]%10[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=%10)=[CH:2][CH:3]=9)=[CH:74][CH:75]=8)=[CH:78][CH:79]=7)[C:21]7[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=7)=[CH:60][CH:59]=6)=[CH:54][CH:53]=5)=[CH:48][CH:47]=4)=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)=[CH:28][CH:29]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 35635834,4''-Diiodo-p-terphenylHCID 23140819N4,N4-di([1,1'-biphenyl]-4-yl)-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine

生成物 1

HCID 59510919N,N'-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4'-yl]-N,N'-diphenyl-4,4''-diamino-p-terphenyl収率 65.9%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

There were mixed 12.68 g (0.022 mole) of N,N-bis(bi-phenyl-4-yl)-N′-phenyl-4,4′-diaminobiphenyl, 5.00 g (0.01 mole) of 4,4″-diiodo-p-terphenyl, 4.14 g (0.030 mole) of anhydrous potassium carbonate, 0.32 g (0.005 mole) of copper powder and 10 ml of n-dodecane, followed by reaction at 195 to 210° C. for 30 hours. The reaction product was extracted with 800 ml of toluene, and the insoluble matter was removed by filtration. Then, the filtrate was concentrated. After the concentration, 100 ml of methanol was added to perform crystallization, and suction filtration was performed to obtain crude crystals. The crude crystals were dissolved in 300 ml of toluene under reflux, and allowed to cool down to 45° C. Then, 300 ml of ethyl acetate was added dropwise to perform crystallization, thereby obtaining crystals. N,N′-bis[4-{bis(biphenyl-4-yl)amino}biphenyl-4′-yl]-N,N′-diphenyl-4,4″-diamino-p-terphenyl was obtained in an amount of 9.43 g. The yield was 65.9%, and the HPLC purity was 94.7%.

後処理

  1. customfollowed by reaction at 195 to 210° C. for 30 hours
  2. extractionThe reaction product was extracted with 800 ml of toluene
  3. customthe insoluble matter was removed by filtration
  4. concentrationThen, the filtrate was concentrated
  5. concentrationAfter the concentration, 100 ml of methanol
  6. additionwas added
  7. customcrystallization, and suction filtration
  8. customto obtain crude crystals
  9. temperatureunder reflux
  10. customcrystallization
  11. customobtaining crystals

出典と根拠

ORDレコード
ord-4ad7474df4284c278aacb13870baf970
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07807274B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート