Potassium Iodide → Phenyl 4-{2-[(3-methylphenyl)amino]-2-oxoethoxy}benzoate

HRID 2377257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377257
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[CH:10][CH:11]=1)=[O:4].[OH:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:12][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])=[CH:16][CH:15]=2)[CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 87250PhenylparabenHCID 2963252-chloro-N-(3-methylphenyl)acetamide

Produkt 1

HCID 69202349Phenyl 4-{2-[(3-methylphenyl)amino]-2-oxoethoxy}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-N-m-tolyl-acetamide (580 mg, 3.16 mmol) and phenyl 4-hydroxybenzoate (677 mg, 3.16 mmol) in acetone (20 mL) was added potassium carbonate (502 mg, 3.63 mmol) and potassium iodide (26 mg, 0.16 mmol) and the mixture was heated to reflux overnight. The mixture was concentrated under vacuum, water was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (2:1) as eluent to provide the desired product. MS (DCI-NH3): m/z 379 (M+NH4)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated under vacuum, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-636f26f27ff34dc5a9db4d51eb006549
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468371B2

Notizen zur Reaktion

Wird geladen…