Phosphorus oxychloride → HCID 68867784, compound

HRID 1986603Notes

Reaction equation

HRID 1986603 reaction equation
[CH3:1][O:2][N:3]1[CH:20]=[C:6]2[CH:7]=[N:8][C:9]3[CH:14]=[C:13]([CH3:15])[C:12](=O)[N:11]([CH2:17][CH2:18][CH3:19])[C:10]=3[N:5]2[CH2:4]1.P(Cl)(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[Cl:23][C:14]1[C:9]2[N:8]=[CH:7][C:6]3[N:5]([CH2:4][N:3]([O:2][CH3:1])[CH:20]=3)[C:10]=2[N:11]([CH2:17][CH2:18][CH3:19])[CH2:12][C:13]=1[CH3:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68869464HCID 68869464, compound

Product 1

HCID 68867784HCID 68867784, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 27 g 8-methoxy-3-methyl-1-propyl-imidazo[1,5-a]-pyrido[3,2-e]-pyrazinone and 225 ml phosphorus oxychloride were heated to reflux for 8 hrs. To the cooled mixture 250 ml of toluene were added and then 350 ml of the liquid were distilled off. Subsequently the same procedure was performed with 150 ml toluene but 250 ml of the liquid were distilled off. The reaction mixture was allowed to cool at room temperature and then poured in a mixture of 500 g ice/500 ml water. After 30 minutes the mixture was extracted with 250 ml of dichloromethane for two times. The dichloromethane layer was then washed with 500 ml water then with sodium carbonate (3% in water) and after that with 500 ml water. The organic layer was dried with sodium sulfate. After removal of the sodium sulfate and evaporation of the dichloromethane the crude product was dried in a dry box with vacuum (40° C.).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 8 hrs
  3. distillation350 ml of the liquid were distilled off
  4. distillationwere distilled off
  5. additionpoured in a mixture of 500 g ice/500 ml water
  6. extractionAfter 30 minutes the mixture was extracted with 250 ml of dichloromethane for two times
  7. washThe dichloromethane layer was then washed with 500 ml water
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. customAfter removal of the sodium sulfate and evaporation of the dichloromethane the crude product
  10. customwas dried in a dry box with vacuum (40° C.)

Sources & evidence

ORD record
ord-063695401b7a4c6385b76e89e7bdf7b6
Source dataset
uspto-grants-2009_06
Patent number
US07550465B2

Reaction notes

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