Phosphorus oxychloride → HCID 22617793, compound

HRID 842057Notes

Reaction equation

HRID 842057 reaction equation
[N+:1]([C:4]1[C:5](=O)[NH:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135216835-Nitro-2-phenylpyrimidin-4(3H)-one

Product 1

HCID 22617793HCID 22617793, compoundYield 86%

Conditions

Temperature
90 °C

Procedure

A mixture of 5-nitro-2-phenyl-4(3H)-pyrimidinone (6 g) and phosphorus oxychloride (8.5 g) is stirred at 90° C. for four hours. After cooling, the reaction mixture is concentrated under reduced pressure, and the residue is dissolved in chloroform. To the mixture is added ice-water, and the mixture is stirred. The mixture is neutralized with 1N aqueous sodium hydroxide solution, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is recrystallized from ethanol to give the desired compound (5.6 g).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in chloroform
  4. additionTo the mixture is added ice-water
  5. stirringthe mixture is stirred
  6. customthe chloroform layer is separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-044eb27cac414ad1af908fb183ff90f7
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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