Phosphorus oxychloride → 2-Chloro-5-pentylpyrimidine

HRID 2267978Notes

Reaction equation

HRID 2267978 reaction equation
O[C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178442226HCID 178442226, compound

Product 1

HCID 167565262-Chloro-5-pentylpyrimidine

Procedure

In 500 ml of phosphorus oxychloride was added 120.4 g (0.724 mol) of the 2-hydroxy-5-pentylpyrimidine described above, and heated to reflux for 5 hours. Excess amount of phosphorus oxychloride was distilled off under a reduced pressure, and the residue was added into an ice water. The product was extracted with toluene, and the extract was washed with aqueous solution of 2N aqueous solution of sodium hydroxide and water in turn, and dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue was purified by distillation to obtain 76.3 g (0.413 mol) of 2-chloro-5-pentylpyrimidine. Yield of this product was 57%.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. distillationExcess amount of phosphorus oxychloride was distilled off under a reduced pressure
  4. additionthe residue was added into an ice water
  5. extractionThe product was extracted with toluene
  6. washthe extract was washed with aqueous solution of 2N aqueous solution of sodium hydroxide and water in turn
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under a reduced pressure
  9. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-27e4943b5ef841a2a4fa575244a60e9f
Source dataset
uspto-grants-2001_12
Patent number
US06326065B1

Reaction notes

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