Phosphorus oxychloride → 6-Chloro-1,3-dimethyl-2-oxo-4-dicyanomethylenepyrimidine

HRID 648890Notes

Reaction equation

HRID 648890 reaction equation
[C:1]([CH:3]([C:14]#[N:15])[C:4]1[N:9]([CH3:10])[C:8](=[O:11])[N:7]([CH3:12])[C:6](=O)[CH:5]=1)#[N:2].P(Cl)(Cl)([Cl:18])=O>O>[Cl:18][C:6]1[N:7]([CH3:12])[C:8](=[O:11])[N:9]([CH3:10])[C:4](=[C:3]([C:14]#[N:15])[C:1]#[N:2])[CH:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136847646-Dicyanomethyl-1,3-dimethyluracil

Product 1

HCID 139077676-Chloro-1,3-dimethyl-2-oxo-4-dicyanomethylenepyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6.1 g (0.03 mol) of the resulting 6-dicyanomethyl-1,3-dimethyluracil was added 1.5 ml of water, and 40 ml of phosphorus oxychloride was added dropwise thereto. After heating the mixture at reflux for 1.5 hours, the phosphorus oxychloride was removed by distillation under normal pressure, and the residue was poured onto ice. The precipitated crystals were collected by filtration. The filtrate was extracted three times with chloroform and dried over anhydrous sodium sulfate. The chloroform was distilled away and the resulting residue was combined with the above obtained crystals. Recrystallization from water-methanol yielded 6.15 g of 6-chloro-1,3-dimethyl-2-oxo-4-dicyanomethylenepyrimidine.

Workup

  1. additionwas added dropwise
  2. temperatureAfter heating the mixture
  3. temperatureat reflux for 1.5 hours
  4. customthe phosphorus oxychloride was removed by distillation under normal pressure
  5. additionthe residue was poured onto ice
  6. filtrationThe precipitated crystals were collected by filtration
  7. extractionThe filtrate was extracted three times with chloroform
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe chloroform was distilled away
  10. customabove obtained crystals
  11. customRecrystallization from water-methanol

Sources & evidence

ORD record
ord-78728455942a4c7eb0362ff3a7e91022
Source dataset
uspto-grants-1988_04
Patent number
US04737442

Reaction notes

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