Phosphorus oxychloride → HCID 23324650, compound

HRID 1380830Notes

Reaction equation

HRID 1380830 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[C:7](O)[N:6]=[C:5]([CH:10]([CH3:12])[CH3:11])[N:4]=1.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:7]1[N:6]=[C:5]([CH:10]([CH3:12])[CH3:11])[N:4]=[C:3]([CH2:2][Cl:1])[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178440239HCID 178440239, compound

Product 1

HCID 23324650HCID 23324650, compound

Conditions

Temperature
80 °C

Procedure

12.1 g (0.065 mol) of 4-chloromethyl-6-hydroxy-2-isopropyl-pyrimidine are suspended in 50 ml of phosphorus oxychloride and the suspension is heated to 80° C. for 30 minutes under nitrogen, the crystalline starting material dissolving gradually. The excess phosphorus oxychloride is then distilled off at 40°-60° C. under reduced pressure. The residue is poured on to ice-water, the pH-value of the mixture is brought to 7 by the addition of sodium hydroxide and the mixture is extracted three times with diethyl ether. The combined organic extracts are dried over anhydrous sodium sulphate and evaporated under reduced pressure. The dark coloured oily residue is taken up in hot n-hexane and the solution is treated with active carbon. After filtration of the hot mixture through Celite there is obtained 6-chloro-4-chloromethyl-2-isopropyl-pyrimidine as an orange oil which is pure in accordance with thin-layer chromatography. By distillation of this oil under reduced pressure there is obtained a colourless liquid, b.p. 75° C./0.05 mmHg, nD20 1.5226.

Workup

  1. dissolutiondissolving gradually
  2. distillationThe excess phosphorus oxychloride is then distilled off at 40°-60° C. under reduced pressure
  3. additionThe residue is poured on to ice-water
  4. additionthe pH-value of the mixture is brought to 7 by the addition of sodium hydroxide
  5. extractionthe mixture is extracted three times with diethyl ether
  6. dry with materialThe combined organic extracts are dried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. additionthe solution is treated with active carbon
  9. filtrationAfter filtration of the hot mixture through Celite there

Sources & evidence

ORD record
ord-fe05ce75b08e4a8fa66043c43f362e74
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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