Phosphorus oxychloride → HCID 19780215, compound

HRID 2248580Notes

Reaction equation

HRID 2248580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH2:14][CH2:15][CH2:16][C:12]=3[NH:11][C:10](=O)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>C(Cl)(Cl)Cl>[Cl:20][C:10]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[CH2:14][CH2:15][CH2:16][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19780228HCID 19780228, compound

Product 1

HCID 19780215HCID 19780215, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 4-(4-fluorophenyl)-1,5,6,7-tetrahydro-2H-cyclopentapyrimidin-2-one (14.3 g) is added phosphorus oxychloride (60 ml), and the mixture is refluxed for 5 hours. After cooling, the reaction mixture is diluted with chloroform (100 ml), and the mixture is added dropwise to ice-water over a period of 20 minutes. After the mixture is stirred for 30 minutes, the organic layer is separated, washed with water, dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. The residue is dissolved in toluene and subjected to silica gel column chromatography. The fractions eluted with toluene are collected and the product therefrom is recrystallized from ethanol to give the desired compound (13.6 g), m.p. 106°-107° C.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. dissolutionThe residue is dissolved in toluene
  8. washThe fractions eluted with toluene
  9. customare collected
  10. customthe product therefrom is recrystallized from ethanol

Sources & evidence

ORD record
ord-2bf2af1e8c3848c493d12e8c127caa8a
Source dataset
uspto-grants-1991_08
Patent number
US05041443

Reaction notes

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