Phosphorus oxychloride → 2-Chloro-1,10-phenanthroline

HRID 716553

Reaction equation

HRID 716553 reaction equation
C[N:2]1[C:15]2[C:6](=[CH:7][CH:8]=[C:9]3[C:14]=2[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][C:3]1=O.P(Cl)(Cl)([Cl:19])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:19][C:3]1[CH:4]=[CH:5][C:6]2[C:15](=[C:14]3[C:9](=[CH:8][CH:7]=2)[CH:10]=[CH:11][CH:12]=[N:13]3)[N:2]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 35813871-Methyl-1,10-phenanthrolin-2(1H)-one

Product 1

HCID 3551932-Chloro-1,10-phenanthrolineYield 75%

Procedure

Under a stream of argon, to compound (2) (8 g; 38 mmol), phosphorus oxychloride (72 mL) and phosphorus pentachloride (9.8 g; 47.6 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 8 hours, and excess phosphorus oxychloride was removed under reduced pressure. To the resulting reaction concentrate, ice water and concentrated aqueous ammonia were added and the resulting mixture was made alkaline to precipitate crude crystals. The crude crystals were separated by filtration and washed with water, and then dried under reduced pressure to give 6.1 g (yield: 75%) of the title compound (3).

Workup

  1. customThe resulting reaction mixture
  2. temperaturerefluxed for 8 hours
  3. customexcess phosphorus oxychloride was removed under reduced pressure
  4. customTo the resulting reaction
  5. concentrationconcentrate
  6. additionice water and concentrated aqueous ammonia were added
  7. customto precipitate crude crystals
  8. customThe crude crystals were separated by filtration
  9. washwashed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-cbdf28e7d2ab48edafa77d6f502aa9d8
Source dataset
uspto-grants-2015_11
Patent number
US09187690B2

Linked notes

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