Phosphorus oxychloride → HCID 19876782, compound

HRID 1440449Notes

Reaction equation

HRID 1440449 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([C:15]([F:18])([F:17])[F:16])[N:3]=1.P(Cl)(Cl)([Cl:21])=O>CN(C)C1C=CC=CC=1>[Cl:21][C:6]1[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([C:15]([F:18])([F:17])[F:16])[N:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136102355Ethyl (2-Methyl-6-trifluoromethyl-3H-pyrimidin-4-on-5-yl)acetate

Product 1

HCID 19876782HCID 19876782, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineCatalyst

Procedure

A solution of ethyl (2-methyl-6-trifluoromethyl-3H-pyrimidin-4-on-5-yl)acetate (2.50 g, 9.46 mmol), N,N-dimethylaniline (3 drops), and phosphorus oxychloride (35 mL) was heated under reflux for 4.5 h. The mixture was concentrated, cooled, and ice water was added. Solid KOH was added to neutralize the mixture and it was extracted with ether. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give 2.61 g (98%) of product as a yellow oil.

Workup

  1. temperatureunder reflux for 4.5 h
  2. concentrationThe mixture was concentrated
  3. temperaturecooled
  4. additionice water was added
  5. additionSolid KOH was added
  6. extractionwas extracted with ether
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b51bdecd4bc84b8daad1083cc9a3b4c0
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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