Ethyl Acetate → HCID 15372699, compound

HRID 394681Notes

Reaction equation

HRID 394681 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:14]([C:23]([NH2:25])=O)[O:13][C:12]=2[CH:26]=1.CCOC(C)=O>N1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:14]([C:23]#[N:25])[O:13][C:12]=2[CH:26]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 15372696HCID 15372696, compound

Product 1

HCID 15372699HCID 15372699, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.9 ml (7.5 mmol) of phosphorus oxychloride are slowly added to a solution of 0.24 g (1.5 mmol) of the amide obtained in Step A in 5 ml of anhydrous pyridine. The reaction medium is heated at reflux for 1 hour under an inert atmosphere and then allowed to cool. After evaporation of the solvent in vacuo, the residue is taken up in dichloromethane and then 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 residue obtained is passed over a silica column (eluant: AcOEt/PE: 25/75) to yield the title nitrile in the form of a white solid.

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 1 hour under an inert atmosphere
  3. temperatureto cool
  4. customAfter evaporation of the solvent in vacuo
  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
  9. customThe residue obtained

Sources & evidence

ORD record
ord-f79280caf536460a8e8a89096767a543
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

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