Phosphorus oxychloride → HCID 19876782, compound

HRID 1886058Notes

Reaction equation

HRID 1886058 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>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C:5]1[C:6]([Cl:21])=[N:7][C:2]([CH3:1])=[N:3][C:4]=1[C:15]([F:18])([F:17])[F:16])[CH3:14]

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-4ce6b241d2364fe6b80b8432975a3aa5
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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