Phosphorus oxychloride → HCID 15372700, compound

HRID 394679Notes

Reaction equation

HRID 394679 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12]2[O:13][C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[O:16][C:17]=2[C:18]([NH2:20])=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.ClCCl>[C:6]1([C:12]2[O:13][C:14]3[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=3[O:16][C:17]=2[C:18]#[N:20])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 15372697HCID 15372697, compound

Product 1

HCID 15372700HCID 15372700, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

3.59 ml (30 mmol) of phosphorus oxychloride are slowly added to a solution of 1.52 g (6 mmol) of the amide obtained in Step A in 15 ml of anhydrous pyridine. The medium is then heated at reflux for 2 hours under argon and then allowed to cool. After evaporation of the solvent in vacuo, the residue obtained is diluted with dichloromethane; the organic phase is then hydrolysed with a saturated solution of sodium hydrogen carbonate. The aqueous phase is extracted with dichloromethane; the organic phase is then dried over magnesium sulphate. The solvent is then evaporated under reduced pressure. Chromatography on a silica column (eluant: AcOEt/PE: 40/60) allows the title nitrile to be obtained in the form of a white solid.

Workup

  1. temperatureThe medium is then heated
  2. temperatureat reflux for 2 hours under argon
  3. temperatureto cool
  4. customAfter evaporation of the solvent in vacuo
  5. customthe residue obtained
  6. extractionThe aqueous phase is extracted with dichloromethane
  7. dry with materialthe organic phase is then dried over magnesium sulphate
  8. customThe solvent is then evaporated under reduced pressure
  9. customto be obtained in the form of a white solid

Sources & evidence

ORD record
ord-3f280d231cb447e0a97a0b862711ec09
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

Loading…