Water → 2-(4-(Benzo[d]thiazol-2-yl)phenyl)-4,7-diphenyl-1,10-phenanthroline

HRID 2354521Notes

Reaction equation

HRID 2354521 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:22]1([C:28]2[C:41]3[C:32](=[C:33]4[C:38](=[CH:39][CH:40]=3)[C:37]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:36][CH:35]=[N:34]4)[N:31]=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C1COCC1>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:35]2[CH:36]=[C:37]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:38]3[C:33](=[C:32]4[C:41](=[CH:40][CH:39]=3)[C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:29][CH:30]=[N:31]4)[N:34]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 23206022-(4-Bromophenyl)benzothiazoleHCID 178418339Butyllithium

Product 1

HCID 593813772-(4-(Benzo[d]thiazol-2-yl)phenyl)-4,7-diphenyl-1,10-phenanthrolineYield 41.91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a three-necked flask of 250 ml, 1.63 g (5.6 mmol) of 2-(4-bromophenyl)benzo[d]thiazole and 70 ml of THF were charged, then 3.5 ml (5.6 mmol) n-butyllithium (1.6M in Hexane solution) was dropped under stirring at −78° C. in a nitrogen atmosphere. The mixture was stirred for one hour at −78° C., and a solution of 1.86 g (5.6 mmol) 4,7-diphenyl-1,10-phenanthroline in 30 ml THF was dropped. Then the mixture was stirred at room temperature for overnight and was added with water. The organic layer was extracted with Dichloromethane and dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation. The product was purified by column chromatography on alumina using Dichloromethane/Hexane as eluent and dried in vacuo, obtaining white powder compound 1.27 g (yield of 41.91%), MS (m/z, FAB+) 541.6.

Workup

  1. stirringThe mixture was stirred for one hour at −78° C.
  2. stirringThen the mixture was stirred at room temperature for overnight
  3. extractionThe organic layer was extracted with Dichloromethane
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was removed by rotary evaporation
  6. customThe product was purified by column chromatography on alumina
  7. customdried in vacuo

Sources & evidence

ORD record
ord-48315c192d984793b0df4b519f21e140
Source dataset
uspto-grants-2010_07
Patent number
US07754348B2

Reaction notes

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