6(5H)-Phenanthridinone → 5-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-5H-phenanthridin-6-one

HRID 523450

反応式

HRID 523450 の反応式
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:17]1[CH:18]=[C:19]([C:23]2[N:28]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:26]=[C:25]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:24]=2)[CH:20]=[CH:21][CH:22]=1.N1C=CC=CC=1C(=O)CC(C1C=CC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Cu](I)I>[C:35]1([C:25]2[N:24]=[C:23]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=3)[N:28]=[C:27]([C:29]3[CH:34]=[C:33]([N:6]4[C:7](=[O:15])[C:8]5[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:14]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]4=5)[CH:32]=[CH:31][CH:30]=3)[N:26]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

8

反応物 4

HCID 18536(5H)-PhenanthridinoneHCID 11430Potassium CarbonateHCID 27284941,3-Di(2-pyridyl)-1,3-propanedioneHCID 589433022-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine

生成物 1

HCID 867326655-[3-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenyl]-5H-phenanthridin-6-one

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

20 g (102 4 mmol) of 5H-phenanthridin-6-one, 43 g (112 mmol) of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 2.3 g (10 2 mmol) of 1,3-bis[2-pyridyl]-1,3-propanedione, 28.3 g (204 mmol) of potassium carbonate and 1.9 g (10.2) of copper iodide are stirred under reflux in 1000 ml of DMF for 90 h. The solution is diluted with water and extracted twice with ethyl acetate, the combined organic phases are dried over Na2SO4, evaporated in a rotary evaporator and purified by chromatography (EtOAc/hexane: 2/3). The residue is recrystallised from toluene and from dichloromethane and finally sublimed in a high vacuum, purity is 99.9%. The yield is 31 g (62 mmol), corresponding to 61% of theory.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe combined organic phases are dried over Na2SO4
  3. customevaporated in a rotary evaporator
  4. custompurified by chromatography (EtOAc/hexane: 2/3)
  5. customThe residue is recrystallised from toluene and from dichloromethane

出典と根拠

ORDレコード
ord-e7ed437354c74910853f4256e480fb4c
出典データセット
uspto-grants-2016_05
特許番号
US09337430B2

関連ノート

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