Phosphorus oxychloride → 2,9-Di-tert-butyl-6-chlorophenanthridine

HRID 1097146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097146
[C:1]([CH:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][N:15]=2)[CH:12]=[CH:11][C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9]3)[C:6]1=O)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:25].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]3[C:13](=[C:14]([Cl:25])[N:15]=2)[CH:12]=[CH:11][C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9]3)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 668135942,9-Di-t-butylphenanthridinone

Produkt 1

HCID 574376592,9-Di-tert-butyl-6-chlorophenanthridineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The above 2,9-di-t-butylphenanthridinone (3.0 g, 9.7 mmole) was added to a reaction flask containing phosphorus pentachloride (3.0 g, 14.6 mmole) and 50 mL of phosphoryl chloride. The reaction mixture was refluxed overnight, cooled to room temperature and diluted with toluene. The excess phosphoryl chloride and toluene were removed by a rotary evaporator. The residue was dissolved into ethyl acetate and washed with distilled water followed by brine. The solvent layer was dried over magnesium sulfate, filtered and concentrated to give the desired 2,9-di-tert-butyl-6-chlorophenanthridine (3.0 grams, 98%) as an off white solid. The product was confirmed by GC Mass Spec and not purified further but used directly in the next step.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe excess phosphoryl chloride and toluene were removed by a rotary evaporator
  3. dissolutionThe residue was dissolved into ethyl acetate
  4. washwashed with distilled water
  5. dry with materialThe solvent layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec5e3501bb59436fa29c1786d24b8627
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08142909B2

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