Phosphorus oxychloride → HCID 57437660, compound

HRID 1618465Notes

Reaction equation

HRID 1618465 reaction equation
[CH3:1][C:2]1[C:15]2[C:6](=[CH:7][N:8]=[C:9]3[C:14]=2[C:13](=O)[CH2:12][CH:11]=[CH:10]3)[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:18].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:18][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:6]=1[CH:5]=[CH:4][CH:3]=[C:2]3[CH3:1])[CH:13]=[CH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 66813488HCID 66813488, compound

Product 1

HCID 57437660HCID 57437660, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above compound, 10-methyl-phenanthridinone (4.0 grams, 19 mmole) was added to a reaction flask containing phosphorus pentachloride (6.0 grams, 0.29 mole) and phosphoryl chloride (50 mL). The reaction mixture was refluxed for 4 hours, 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 6-chloro-10-methylphenanthridine (4.1 grams, 95%) as an off-white solid. The product was confirmed by Mass Spec and NMR and not purified further but used directly in the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  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-81078d5c84f743dd998fc951c81fa985
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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