Aniline → N,N,N'-triphenyl-4-phenylenediamine

HRID 634535

反応式

HRID 634535 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCCCCC.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:4]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

参加物

8

反応物 5

HCID 6115AnilineHCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 6428384-BromotriphenylamineHCID 23676156Sodium t-butoxide

生成物 1

HCID 161288N,N,N'-triphenyl-4-phenylenediamine収率 42%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

0.56 g (6 mmol) of 4-bromotriphenylamine, 0.35 g (0.6 mmol) of bis(dibenzylideneacetone)palladium(0), and 0.58 g (6 mmol) of sodium-tert-butoxide were put into a 100 mL three neck flask, and 5 mL of toluene was added thereto. After nitrogen was substituted for the content of the flask, 0.56 g (6 mmol) of aniline and 0.37 mL (1.8 mmol) of a hexane solution (10 wt %) of tri-tert-butylphosphine were added. This mixture was stirred for 5 hours at 80° C. to be reacted. After the reaction, the reaction was completed by adding a saturated saline solution to the reaction mixture, and an aqueous layer was extracted by approximately 100 mL of ethyl acetate to be separated from an organic layer. The organic layer was dried with magnesium sulfate and filtered. A solid that was obtained by concentrating the filtrate was purified by silica column chromatography, whereby 0.24 g of a light yellow powder solid of DPA that is an object was obtained in the yield of 42% (Synthesis Scheme (i-2)). For the column purification, a mixed solvent of ethyl acetate:hexane=1:20 was used as a developing solvent.

後処理

  1. additionwas added
  2. additionwere added
  3. customto be reacted
  4. customAfter the reaction
  5. additionby adding a saturated saline solution to the reaction mixture
  6. extractionan aqueous layer was extracted by approximately 100 mL of ethyl acetate
  7. customto be separated from an organic layer
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. customA solid that was obtained
  11. concentrationby concentrating the filtrate
  12. customwas purified by silica column chromatography, whereby 0.24 g of a light yellow powder solid of DPA that
  13. customwas obtained in the yield of 42% (Synthesis Scheme (i-2))
  14. customFor the column purification

出典と根拠

ORDレコード
ord-1691873a788845f5b96f46aaca1dabf3
出典データセット
uspto-grants-2016_04
特許番号
US09324951B2

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