Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide

HRID 70260

Reaktionsgleichung

Reaktionsgleichung von HRID 70260
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O[CH2:26][CH2:27][Cl:28])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 671598185-(3-Hydroxyphenyl)-2-thiophenecarboxamide

Produkt 1

HCID 582762485-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-(3-Hydroxyphenyl)-2-thiophenecarboxamide (0.31 g, 1.41 mmol), 2-chloroethyl p-toluenesulfonate (1.327 g, 5.65 mmol) and potassium carbonate (0.782 g, 5.65 mmol) in 20 ml of acetonitrile were heated to reflux for 15 h. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (50 to 80% ethyl acetate in hexanes) to give the title compound as a white solid.

Aufarbeitung

  1. temperatureto reflux for 15 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by silica gel column chromatography (50 to 80% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c81fcc60d7d54774b3aa20fb85f374c1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822518B2

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