Phosphorus oxychloride → HCID 19903221, compound

HRID 2372313Notes

Reaction equation

HRID 2372313 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]([F:24])([F:23])[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([NH2:22])=O)[CH2:16][CH2:15]2)[CH:11]=[CH:10][N:9]=1>CN(C=O)C>[F:24][C:7]([F:6])([F:23])[C:8]1[N:13]=[C:12]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]#[N:22])[CH2:18][CH2:19]2)[CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19008882HCID 19008882, compound

Product 1

HCID 19903221HCID 19903221, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (22 mL) was added with stirring to DMF (220 mL). The exothermic reaction mixture turned deep red, and compound VI (23.20 g, 85 mmol) was added. The mixture was cooled in a water bath and stirred for 20 hr. The DMF was then removed under vacuum and the residue was dissolved in methylene chloride (300 mL). Saturated aqueous sodium carbonate (ca 200 mL) was added to the solution with ice bath cooling until no more bubbling was observed. The methylene chloride layer was separated and concentrated in vacuo. The residue was recrystallized from hexanes-ethyl acetate to give the crystalline product (19.0 g, 87%).

Workup

  1. temperatureThe mixture was cooled in a water bath
  2. customThe DMF was then removed under vacuum
  3. dissolutionthe residue was dissolved in methylene chloride (300 mL)
  4. additionSaturated aqueous sodium carbonate (ca 200 mL) was added to the solution with ice bath
  5. temperaturecooling until
  6. customno more bubbling
  7. customThe methylene chloride layer was separated
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from hexanes-ethyl acetate

Sources & evidence

ORD record
ord-4488d9743893468694bff59b3c86a10d
Source dataset
uspto-grants-1992_03
Patent number
US05098904

Reaction notes

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