Hydrochloric Acid → HCID 178517445, compound

HRID 1710473Notes

Reaction equation

HRID 1710473 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.[NH2:16][C:17]([NH2:19])=[O:18].Cl>C(O)C>[OH:18][C:17]1[N:19]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1176UreaHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedione

Product 1

HCID 178517445HCID 178517445, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,4,4-Trifluoro-1-phenyl-1,3-butanedione (10.8 g) and urea (6.01 g) were dissolved in ethanol (25 mL) and concentrated hydrochloric acid (5 mL) was added. The mixture was heated under reflux for 2.5 hr. The reaction solution was concentrated under reduced pressure, and water was added. The mixture washed with chloroform. A saturated a aqueous sodium hydrogen carbonate solution was added to the a aqueous layer and the precipitate was collected by filtration to give 2-hydroxy-4-phenyl-6-trifluoromethylpyrimidine (5.03 g) as a pale-pink crystalline powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 hr
  3. concentrationThe reaction solution was concentrated under reduced pressure, and water
  4. additionwas added
  5. washThe mixture washed with chloroform
  6. additionA saturated a aqueous sodium hydrogen carbonate solution was added to the a aqueous layer
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-910aefe0356e4ec48c0a93ddf9f94c5f
Source dataset
uspto-grants-2010_09
Patent number
US07790725B2

Reaction notes

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