Sodium Carbonate → 2-[3,5-Bis(1,10-phenanthrolin-2-yl) phenyl]-4,6-diphenyl-1,3,5-triazine

HRID 1773055

Reaktionsgleichung

Reaktionsgleichung von HRID 1773055
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[C:26]([C:39]3[N:44]=[C:43]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:42]=[C:41]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:40]=3)[CH:27]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:29]=2)O1.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C.C1(C)C=CC=CC=1>[N:3]1[C:4]2[C:13](=[CH:12][CH:11]=[C:10]3[C:5]=2[N:6]=[CH:7][CH:8]=[CH:9]3)[CH:14]=[CH:15][C:2]=1[C:28]1[CH:27]=[C:26]([C:39]2[N:40]=[C:41]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[N:42]=[C:43]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:44]=2)[CH:25]=[C:24]([C:7]2[CH:8]=[CH:9][C:10]3[C:5](=[C:4]4[C:13](=[CH:12][CH:11]=3)[CH:14]=[CH:15][CH:2]=[N:3]4)[N:6]=2)[CH:29]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 3551932-Chloro-1,10-phenanthrolineHCID 433294Lithium ChlorideHCID 583826222-[3,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine

Produkt 1

HCID 904014662-[3,5-Bis(1,10-phenanthrolin-2-yl) phenyl]-4,6-diphenyl-1,3,5-triazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a stream of argon, 4.26 g of 2-chloro-1,10-phenanthroline, 4.67 g 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine, 1.06 g of lithium chloride and 767 mg of tetrakis(triphenylphosphine) palladium were suspended in a toluene (200 mL)/ethanol (50 mL) mixed solvent. 33.2 mL of a 2.0 M aqueous sodium carbonate solution was added in the suspension, and the mixture was stirred at 100° C. for 94 hours. Then the reaction mixture was left to be cooled to room temperature and distilled under a reduced pressure to remove low-boiling point ingredients. The obtained residue was purified by alumina column chromatography using a hexane/chloroform (1:2 to 0:1) mixed solvent as a developing solvent, and then recrystallized from a dichloromethane/methanol mixed solvent to give 4.76 g of target 2-[3,5-bis(1,10-phenanthrolin-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine as a white powder (yield, 86%).

Aufarbeitung

  1. additionmixed solvent
  2. waitThen the reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. distillationdistilled under a reduced pressure
  5. customto remove low-boiling point ingredients
  6. customThe obtained residue was purified by alumina column chromatography
  7. additionmixed solvent as a developing solvent
  8. customrecrystallized from a dichloromethane/methanol mixed solvent
  9. customto give

Quellen und Nachweise

ORD-Eintrag
ord-dc4eb7d77c3a4f8a860a8f94a1686b49
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09252368B2

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