Water → N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)ethanesulfonamide

HRID 30604

Reaktionsgleichung

Reaktionsgleichung von HRID 30604
[F:1][CH:2]([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=2)[NH2:15])=[CH:6][CH:5]=1.N1C=CC=CC=1.[CH2:26]([S:28](Cl)(=[O:30])=[O:29])[CH3:27].O>C(Cl)Cl>[F:1][CH:2]([F:19])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([NH:15][S:28]([CH2:26][CH3:27])(=[O:30])=[O:29])[CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 574358643-{[4-(Difluoromethoxy)phenyl]ethynyl}aniline

Produkt 1

HCID 59790328N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)ethanesulfonamideAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A cold (0° C.) solution of 3-{[4-(difluoromethoxy)phenyl]ethynyl}aniline (0.5 g, 1.93 mmol) and pyridine (0.31 mL, 3.80 mmol) in CH2Cl2 was treated dropwise with ethylsulfonyl chloride (0.27 mL, 2.89 mmol). The mixture was stirred for 5 hours, poured into water and extracted with EtOAc/ethyl ether 1/1. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue on silica gel (Biotage) using hexanes/EtOAc (3/1) as the eluting solvent gave N-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)ethanesulfonamide as a yellow oil (0.62 g).

Aufarbeitung

  1. extractionextracted with EtOAc/ethyl ether 1/1
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the resultant residue on silica gel (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-a9064075b6f744c19024d33c4e103b56
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

Verknüpfte Notizen

Wird geladen…