4-Phenylbenzoyl chloride → HCID 58979977, compound

HRID 1180680Notes

Reaction equation

HRID 1180680 reaction equation
N1[C:5]([C:6]2[CH:19]=C[C:17]3[C:8](=[C:9]4[C:14](=CC=3)C=CC(C3NN=NN=3)=N4)[N:7]=2)=[N:4][N:3]=N1.[C:25]1([C:31]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:31]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:39]=[CH:38][C:34]([C:35]2[O:36][C:5]([C:6]3[CH:19]=[CH:14][C:9]4[C:8](=[C:17]5[C:9](=[CH:8][CH:17]=4)[CH:14]=[CH:19][C:6]([C:5]4[O:36][C:35]([C:34]6[CH:38]=[CH:39][C:31]([C:25]7[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=7)=[CH:32][CH:33]=6)=[N:3][N:4]=4)=[N:7]5)[N:7]=3)=[N:4][N:3]=2)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 841514-Phenylbenzoyl chlorideHCID 178419810HCID 178419810, compound

Product 1

HCID 58979977HCID 58979977, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, a mixture of 13 g (0.045 mol) 2,9-bis-(1H-tetrazol-5-yl)-[1,10]phenanthroline and 390 ml pyridine was added to a 250 ml three-necked flask. The mixture was then heated to 50° C., and 46 g (0.21 mol) 4-phenylbenzoyl chloride was then added drop by drop. After the adding, the mixture solution was heated to reflux (110° C.) and stirred overnight. After completion of reaction, as shown in scheme 2, the reaction mixture was cooled to room temperature, filtered. Finally, solids were separated, washed by 100 ml methanol, filtered and purified by column chromatography to obtain white products 2,9-bis-(5-biphenyl-4-yl-[1,3,4]oxadiazol-2-yl)-[1,10]phenanthroline 11 g (0.018 mol, yield 40%). MS(m/z, FAB+), 620, 291, 248, 233, 208, 156, 130, 105.

Workup

  1. additionwas added to a 250 ml three-necked flask
  2. temperatureAfter the adding, the mixture solution was heated
  3. temperatureto reflux (110° C.)
  4. customAfter completion of reaction
  5. temperaturethe reaction mixture was cooled to room temperature
  6. filtrationfiltered
  7. customFinally, solids were separated
  8. washwashed by 100 ml methanol
  9. filtrationfiltered
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-839940281542488f9445d8b8c356b2a4
Source dataset
uspto-grants-2007_10
Patent number
US07282586B1

Reaction notes

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