Thionyl Chloride → Methyl 3-(4-pentenoylamino)benzoate

HRID 2334

Reaktionsgleichung

Reaktionsgleichung von HRID 2334
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[C:12](Cl)(=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16].C(O)(=O)CCC=C.S(Cl)(Cl)=O>C(Cl)Cl.N1C=CC=CC=1>[C:12]([NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:11])(=[O:17])[CH2:13][CH2:14][CH:15]=[CH2:16]

Komponenten

7

Edukt 4

HCID 24386Thionyl ChlorideHCID 611384-Pentenoic acidHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 42284934-Pentenoyl chloride

Produkt 1

HCID 10775994Methyl 3-(4-pentenoylamino)benzoateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%).

Aufarbeitung

  1. customat 0° C
  2. customevaporated
  3. customazeotroped with DCM)
  4. additionwas added dropwise in DCM (3 ml)
  5. customThe mixture was evaporated
  6. custompartitioned between EtOAc and 1M HCl
  7. washThe organic portion was washed with 5% KHCO3 and brine
  8. filtrationfiltered (Whatman® 1PS, phase separator)
  9. customevaporated
  10. customThe residue was chromatographed (eluant 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-21d973d5e9c342b28599ca4532af6af7
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728829

Verknüpfte Notizen

Wird geladen…