Water → HCID 70692250, compound

HRID 576740Notes

Reaction equation

HRID 576740 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=1.[NH2:17][C:18](N)=[O:19].O>C(O)(=O)C>[F:15][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][C:12](=[O:14])[NH:17][C:18]2=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1176UreaHCID 172449643-(3-Trifluoromethylphenylamino)propionic acid

Product 1

HCID 70692250HCID 70692250, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(3-trifluoromethylphenylamino)propanoic acid (2.0 g) (prepared in Reference Example 95) and urea (1.0 g) in acetic acid (20.0 ml) was stirred with heating under reflux for seven hours. To the reaction mixture was water (50 ml) and the resulting mixture was extracted with ethyl acetate (30 ml×3). The organic layer was washed with water (20 ml×2) and saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 1-(3-trifluoromethylphenyl)dihydropyrimidin-2,4(1H,3H)-dione (1.5 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for seven hours
  3. extractionthe resulting mixture was extracted with ethyl acetate (30 ml×3)
  4. washThe organic layer was washed with water (20 ml×2) and saturated saline (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-01e4fb164a7046e0a71844c037b83308
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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