Phosphorus oxychloride → HCID 5295472, compound

HRID 327018Notes

Reaction equation

HRID 327018 reaction equation
O[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178439467HCID 178439467, compound

Product 1

HCID 5295472HCID 5295472, compound

Procedure

The 5-hydroxy-3-isopropyl-1-methylpyrazole (20.5 g) was added in small portions over five minutes to 60 ml of phosphorus oxychloride cooled at 10 C. No significant exotherm resulted and after five minutes the cooling bath was removed. After stirring for one hour, the reaction was heated to 70 C. overnight and then 90 C. for four hours. The cooled reaction was cautiously added to 500 g of ice. The desired product was extracted with two 200 ml portions of ethyl acetate and the combined extracts were concentrated under reduced pressure to yield 13.7 g of the desired product as an oil.

Workup

  1. temperaturecooled at 10 C
  2. customNo significant exotherm resulted and after five minutes the cooling bath
  3. customwas removed
  4. temperaturethe reaction was heated to 70 C
  5. customovernight
  6. waitfor four hours
  7. customThe cooled reaction
  8. extractionThe desired product was extracted with two 200 ml portions of ethyl acetate
  9. concentrationthe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-06a6acd22ef64f19bc8294e252ed5924
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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