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N,N,N'-triphenyl-4-phenylenediamine → HCID 59844173、化合物

HRID 2282792
ノート
印刷プレビュー

反応式

HRID 2282792 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=3.[C:22]1([N:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[C:49]([CH3:52])([O-])[CH3:50].[Na+]>[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:22]1([N:28]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:29]2[CH:34]=[CH:33][C:32]([N:35]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[C:7]5[C:12]([C:13]=4[CH:14]=3)=[CH:11][C:10]([N:35]([C:50]3[CH:49]=[CH:52][CH:41]=[CH:36][CH:37]=3)[C:32]3[CH:33]=[CH:34][C:29]([N:28]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:30][CH:31]=3)=[CH:9][CH:8]=5)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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

6

反応物 3

HCID 161288N,N,N'-triphenyl-4-phenylenediamineHCID 134073473,6-Diiodo-9-phenylcarbazoleHCID 23676156Sodium t-butoxide

生成物 1

HCID 59844173HCID 59844173、化合物収率 75%

試薬・触媒・溶媒 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒
HCID 1140
Toluene
溶媒
2 回

反応条件

温度
80 °C

実験手順

Specifically, 5.44 g (11 mmol) of 3,6-diiodo-9-phenylcarbazole, 9 g (27 mmol) of N-(4-diphenylaminophenyl)-N-phenylamine, 500 mg (0.87 mmol) of bis(dibenzylidene acetone) palladium and 3.35 mg (35 mmol) of sodium tert-butoxide were mixed in a three-neck flask. Nitrogen was substituted for air inside of the three-neck flask. Subsequently, 100 ml of dehydrated toluene was added to the mixture in the three-neck flask. The mixture added with the dehydrated toluene was degassed for about 3 minutes. Then, 4 ml of tri-tert-butyl phosphine (a 10 wt % hexane solution) was added to the mixture and then this mixture was stirred, while heating at 80° C., for 16 hours under nitrogen atmosphere. After the reaction, saturated saline was added and a product was extracted with 200 ml of ethyl acetate. Further, magnesium sulfate was added to the product to remove moisture, and then the magnesium sulfate was filtered to be removed. The filtrate was concentrated, and the concentrated filtrate was dripped in a solvent containing ethyl acetate and hexane with a ratio of 1:10 to be suspended. Afterwards, a supernatant of the suspension was collected. The supernatant was purified by a silica gel column using a solvent containing ethyl acetate and hexane with a ratio of 1:10. The resultant was concentrated to obtain a cream-colored powder. In addition, an insoluble component of the suspension was purified by a silica gel column using a solvent that contains 5:1 toluene and hexane. The resultant was concentrated to obtain a cream-colored powder. The cream-colored powders obtained in the above described manner were target matters. Specifically, 6.5 g of the cream-colored powders in total were obtained and the yield was 75%. The NMR data is shown below. The 1H-NMR (300 MHz, DMSO-d); δ=6.86-6.97 (m, 26H), 7.18-7.36 (m, 14H), 7.35 (d, j=9.0, 2H), 7.52-7.66 (m, 5H), 7.99 (s, 2H). Also, a chart of 1H-NMR is shown in FIG. 15. Also, a chart of an enlarged portion of FIG. 15 in the range of 6.0 ppm and 9.0 ppm is shown in FIG. 16.

後処理

  1. customwas degassed for about 3 minutes
  2. additionThen, 4 ml of tri-tert-butyl phosphine (a 10 wt % hexane solution) was added to the mixture
  3. customAfter the reaction, saturated saline
  4. additionwas added
  5. extractiona product was extracted with 200 ml of ethyl acetate
  6. additionFurther, magnesium sulfate was added to the product
  7. customto remove moisture
  8. filtrationthe magnesium sulfate was filtered
  9. customto be removed
  10. concentrationThe filtrate was concentrated
  11. additioncontaining ethyl acetate and hexane with a ratio of 1:10
  12. customAfterwards, a supernatant of the suspension was collected
  13. customThe supernatant was purified by a silica gel column
  14. additioncontaining ethyl acetate and hexane with a ratio of 1:10
  15. concentrationThe resultant was concentrated
  16. customto obtain a cream-colored powder
  17. customIn addition, an insoluble component of the suspension was purified by a silica gel column
  18. concentrationThe resultant was concentrated
  19. customto obtain a cream-colored powder
  20. customThe cream-colored powders obtained in the

出典と根拠

ORDレコード
ord-1833b61d851749569a6fa8801af2f2bd
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09142783B2

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