Phosphorus oxychloride → 2,9-Dichloro-1,10-phenanthroline

HRID 716556

Reaction equation

HRID 716556 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]([N:15]=1)=[C:13]1[C:8]([CH:9]=[CH:10][C:11](=O)[N:12]1C)=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:20])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:20][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:14]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[CH:3][C:2]([Cl:1])=[N:15]3)[N:12]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 28475409-Chloro-1-methyl-1,10-phenanthrolin-2(1H)-one

Product 1

HCID 3551962,9-Dichloro-1,10-phenanthrolineYield 94%

Procedure

Under a stream of argon, to compound (5) (4.26 g; 17.4 mmol), phosphorus oxy-chloride (39 mL) and phosphorus pentachloride (4.48 g; 21.8 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 7 hours, and then evaporated under reduced pressure to remove phosphorus oxychloride. To the resulting residue, ice water and concentrated aqueous ammonia were added and the resulting reaction mixture was made alkaline. The solids which precipitated out were separated by filtration and washed with water, and then dried under reduced pressure to give 4.06 g (yield: 94%) of the title compound (6).

Workup

  1. customThe resulting reaction mixture
  2. temperaturerefluxed for 7 hours
  3. customevaporated under reduced pressure
  4. customto remove phosphorus oxychloride
  5. additionTo the resulting residue, ice water and concentrated aqueous ammonia were added
  6. customthe resulting reaction mixture
  7. customThe solids which precipitated out
  8. customwere separated by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-544c1f3e9e80496db3a0d92b777526e6
Source dataset
uspto-grants-2015_11
Patent number
US09187690B2

Linked notes

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