Hydrogen Peroxide → HCID 86664968, compound

HRID 1622053Notes

Reaction equation

HRID 1622053 reaction equation
[C:1]1([P:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[N:13]=[C:12]([C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH3:15])[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:34]O>ClCCl>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([C:12]1[N:13]=[C:8]([P:7](=[O:34])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:9]=[CH:10][CH:11]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH3:15]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86664969HCID 86664969, compound

Product 1

HCID 86664968HCID 86664968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.7 g of 2,2′-(1-(6-(diphenylphosphino)pyridin-2-yl)ethane-1,1-diyl)dipyridine were dissolved in 25 ml of dichloromethane and ice-bath cooled. 1.8 ml of hydrogen peroxide (35 wt % in water) were added drop wise and the mixture was stirred overnight at room temperature. The reaction was quenched with 20 ml of saturated ammonium chloride solution and the aqueous layer was extracted three times with dichloromethane. The combined organic layers were washed with brine and dried with magnesium sulphate. The solvent was removed under reduced pressure until the residue starts to foam. The residue crystallised from diethyl ether. After drying in high vacuum 5.1 g (74%) of an off-white solid were obtained. The compound was further purified by gradient sublimation.

Workup

  1. temperatureice-bath cooled
  2. customThe reaction was quenched with 20 ml of saturated ammonium chloride solution
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with magnesium sulphate
  6. customThe solvent was removed under reduced pressure until the residue
  7. customThe residue crystallised from diethyl ether
  8. dry with materialAfter drying in high vacuum 5.1 g (74%) of an off-white solid
  9. customwere obtained
  10. customThe compound was further purified by gradient sublimation

Sources & evidence

ORD record
ord-e6a05751d3a447c28738a7d147ed1067
Source dataset
uspto-grants-2014_07
Patent number
US08778512B2

Reaction notes

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