Phosphorus oxychloride → HCID 15372698, compound

HRID 394674Notes

Reaction equation

HRID 394674 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]=[C:9]([C:12]([NH2:14])=O)[O:8][C:7]=2[CH:15]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]=[C:9]([C:12]#[N:14])[O:8][C:7]=2[CH:15]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 15372695HCID 15372695, compound

Product 1

HCID 15372698HCID 15372698, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.76 g (8.52 mmol) of the amide obtained in Step A and 4.62 g (30 mmol) of phosphorus oxychloride are dissolved in 40 ml of anhydrous pyridine. The reaction medium is then heated at reflux for 1 hour under an inert atmosphere; the solvent is then evaporated in vacuo. The residue obtained is slowly hydrolysed with a saturated solution of sodium hydrogen carbonate; the aqueous phase is then extracted with dichloromethane. The organic phase, dried over magnesium sulphate and then filtered, is concentrate in vacuo. The title nitrile is obtained pure in the form of a white solid after passage over a silica column (eluant: AcOEt/PE: 10/60).

Workup

  1. temperatureThe reaction medium is then heated
  2. temperatureat reflux for 1 hour under an inert atmosphere
  3. customthe solvent is then evaporated in vacuo
  4. customThe residue obtained
  5. extractionthe aqueous phase is then extracted with dichloromethane
  6. dry with materialThe organic phase, dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationis concentrate in vacuo

Sources & evidence

ORD record
ord-94b49823a1214607a82dd2ae0900dfe8
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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