Phosphorus oxychloride → HCID 43654681, compound

HRID 1626452Notes

Reaction equation

HRID 1626452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:17])=O>C1(C)C=CC=CC=1.ClCCl>[Cl:17][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 5505272-(4-Chlorophenyl)-4(3H)-pyrimidinone

Product 1

HCID 43654681HCID 43654681, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-(4-chlorophenyl)pyrimidin-4(3H)-one (100 mg, 0.4840 mmol), suspended in toluene (2 ml), was treated with phosphoryl trichloride (443.0 μl, 4.840 mmol) at ambient temperature. The suspension was heated to reflux at which point the reaction became a colorless solution. After 4 hours, the reaction was cooled to ambient temperature and concentrated in vacuo to afford a white solid. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate. The organics were dried with sodium sulfate, filtered, concentrated, and purified on silica gel. Elution with 2-20% ethyl acetate/hexanes provided the title compound (99 mg, 0.4399 mmol, 90.89% yield) as a white solid.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux at which
  3. concentrationconcentrated in vacuo
  4. customto afford a white solid
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialThe organics were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica gel
  10. washElution with 2-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-979e2128a5b2401c9409f4552db50a06
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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