Phosphorus pentachloride → 4-chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine

HRID 2415026Notes

Reaction equation

HRID 2415026 reaction equation
[I:1][C:2]1[C:3](=O)[NH:4][C:5]([S:12][CH3:13])=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O>[Cl:16][C:3]1[C:2]([I:1])=[C:7]([C:8]([F:11])([F:10])[F:9])[N:6]=[C:5]([S:12][CH3:13])[N:4]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 135804110HCID 135804110, compound

Product 1

HCID 121514194-chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidineYield 98%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

5-Iodo-2-methylthio-6-trifluoromethyl-3H-pyrimidin-4-one (11.8 g) was dissolved in phosphoryl chloride (40 ml) and phosphorous pentachloride (7.9 g) was added at room temperature with stirring. The mixture was refluxed for 3 hr and the phosphoryl chloride was removed under reduced pressure. The residue was poured onto icy water and extracted with chloroform. The chloroform layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 4-chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (12.2 g) as pale brown crystalline solid, mp 55-56° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hr
  2. customthe phosphoryl chloride was removed under reduced pressure
  3. additionThe residue was poured onto icy water
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water and brine
  6. dry with materialrespectively and dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3be79d9ac54043c3a494b194b6770a2e
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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