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

HRID 1618459Notes

Reaction equation

HRID 1618459 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3358d10bd1ee45fca01ecace139cd7c7
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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