Phosphorus oxychloride → HCID 15372698, compound

HRID 428182Notes

Reaction equation

HRID 428182 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 concentrated 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 concentrated in vacuo

Sources & evidence

ORD record
ord-a8b8f3246ee24fe8b7a654b6f851c77c
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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