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Pyridine → N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-chlorobenzenesulfonamide

HRID 1791850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1791850
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH:9]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][C:10]2[CH:9]=[C:8]([NH:7][S:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[Cl:25])(=[O:34])=[O:33])[CH:13]=[CH:12][CH:11]=2)=[CH:22][CH:21]=1)#[N:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 22033543HCID 22033543, Verbindung

Produkt 1

HCID 10873356N-{3-[2-(4-Cyanophenyl)ethoxy]phenyl}-2-chlorobenzenesulfonamideAusbeute 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridine (0.255 mL; 3.15 mmol) was added to a stirred solution of amino-3-[2-(4-cyanophenyl)ethoxy]benzene (0.15 g; 0.629 mmol; from step (ii) above) and 2-chlorobenzenesulfonyl chloride (0.173 mL; 0.818 mmol) in CH2Cl2 (4 mL). After 45 minutes at room temperature the solvent was removed in vacuo. To remove traces of pyridine, EtOH was added and evaporated. The residue was partitioned between water and EtOAc. The organic layer was washed with 0.1M aqueous HCl and brine, dried (Na2SO4) and the solvent removed in vacuo. Purification by flash chromatography (SiO2; toluene:EtOAc (1:0 to 9:1)) afforded 0.095 g (35%) of the sub-title compound.

Aufarbeitung

  1. customAfter 45 minutes at room temperature the solvent was removed in vacuo
  2. customTo remove traces of pyridine, EtOH
  3. additionwas added
  4. customevaporated
  5. customThe residue was partitioned between water and EtOAc
  6. washThe organic layer was washed with 0.1M aqueous HCl and brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customPurification by flash chromatography (SiO2; toluene:EtOAc (1:0 to 9:1))

Quellen und Nachweise

ORD-Eintrag
ord-a07f8c5795414f378ef03facfd4bc52e
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07074820B2

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